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C1CC2=C(C=CC(=C2)F)NC(=O)C1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 7-fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-one |
|---|---|
| IUPAC Name | — |
| CAS Number | 53842-01-6 |
| Database ID | 54106498 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
7-fluoro-1,3,4,5-tetrahydro-1-benzazepin-2-one (CAS 53842-01-6) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 54106498
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-411d37c7d3fe40c1b784b7bcea4428d1Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-102a2dd5872c403599c432ee23609084Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-411d37c7d3fe40c1b784b7bcea4428d1Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (411 mg, 2.3 mmol) (Step A) dissolved in a mixture of 7.9 mL of dry methylene chloride and 1.0 mL of dry tetrahydrofuran was treated with 1.62 mL (1.18 g, 11.6 mmol, 5 eq) of triethylamine and the resulting solution cooled to -15° C. Iodotrimethylsilane (0.66 mL, 932 mg, 4.7 mmol, 2 eq) was added followed by 1.183 g of iodine (4.7 mmol, 2 eq) added in small portions over 5 minutes. The mixture was warmed to room temperature over 5 minutes at which time 15 mL of methylene chloride was added followed by 20 mL of 10% aqueous sodium sulfite. The layers were separated and the organic layer washed with 10% sodium sulfite (3×20 mL). The aqueous layer was further extracted with 20 mL of methylene chloride. The combined extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated to dryness under vacuum. The crude product was chromatographed on silica gel, eluting with methylene chloride/methanol (99:1) to afford 511 mg (1.68 mmol, 73%) of the product. 1H NMR (300MHz, CDCl3): 2.70 (m,3H), 2.93 (m,1H), 4.62 (t,9Hz,1H), 6.95 (m,3H), 7.86 (br s,1H). FAB-MS: calculated for C10H9FINO 305; found 306 (M+H,100%). added in small portions over 5 minutes was added The layers were separated the organic layer washed with 10% sodium sulfite (3×20 mL) The aqueous layer was further extracted with 20 mL of methylene chloride The combined extracts were washed with brine dried over magnesium sulfate filtered concentrated to dryness under vacuum The crude product was chromatographed on silica gel eluting with methylene chloride/methanol (99:1)
Source ID: ord-8353b95d1e4943b1bf124f59cd32115aConditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (411 mg, 2.3 mmol) (Step A) dissolved in a mixture of 7.9 mL of dry methylene chloride and 1.0 mL of dry tetrahydrofuran was treated with 1.62 mL (1.18 g, 11.6 mmol, 5 eq) of triethylamine and the resulting solution cooled to -15° C. Iodotrimethylsilane (0.66 mL, 932 mg, 4.7 mmol, 2 eq) was added followed by 1.183 g of iodine (4.7 mmol, 2 eq) added in small portions over 5 minutes. The mixture was warmed to room temperature over 5 minutes at which time 15 mL of methylene chloride was added followed by 20 mL of 10% aqueous sodium sulfite. The layers were separated and the organic layer washed with 10% sodium sulfite (3×20 mL). The aqueous layer was further extracted with 20 mL of methylene chloride. The combined extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated to dryness under vacuum. The crude product was chromatographed on silica gel, eluting with methylene chloride/methanol (99:1) to afford 511 mg (1.68 mmol, 73%) of the product. 1H NMR (300MHz, CDCl3): 2.70 (m,3H), 2.93 (m,1H), 4.62 (t,9Hz,1H), 6.95 (m,3H), 7.86 (br s,1H). FAB-MS: calculated for C10H9FINO 305; found 306 (M+H,100%). added in small portions over 5 minutes was added The layers were separated the organic layer washed with 10% sodium sulfite (3×20 mL) The aqueous layer was further extracted with 20 mL of methylene chloride The combined extracts were washed with brine dried over magnesium sulfate filtered concentrated to dryness under vacuum The crude product was chromatographed on silica gel eluting with methylene chloride/methanol (99:1)
Source ID: ord-8353b95d1e4943b1bf124f59cd32115aConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium azide 1.1 g (16.92 mmol) was added to a mixture of 6.0 mL of chloroform and 1.1 mL of water at 0° C. Concentrated sulfuric acid (0.44 mL) was added dropwise and the mixture stirred at 0° C. for two hours then filtered. The chloroform layer containing hydrazoic acid was added to a solution of 1.3 g (7.92 mmol) of 6-fluoro-1-tetralone (prepared by the method of Allinger and Jones, J. Org. Chem., 27, 70-76 (1962)) in 4.8 mL of chloroform. Additional sulfuric acid (2.16 mL) was added dropwise with stirring while maintaining the temperature below 40° C. The mixture was stirred at 40° C. for two hours then at room temperature for 16 hours. The mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was added to ice; the resulting recipitate was extracted with methylene chloride (5x). The combined extracts were washed with brine, dried over magnesium sulfate and filtered through a silica plug. Solvents were removed under vacuum to afford 162 mg (0.92 mmol, 11%) of the product. 1H NMR (300MHz, CDCl3): 2.21 (m,2H), 2.32 (t,7Hz,2H), 2.7 (t,7Hz,2H), 6.93 (m,3H), 7.8 (br s,1H). FAB-MS: calculated for C10H10FNO 179; found 180 (M+H,100%). then filtered The chloroform layer containing hydrazoic acid prepared by the method of Allinger and Jones, J with stirring while maintaining the temperature below 40° C The mixture was stirred at 40° C. for two hours at room temperature for 16 hours The mixture was transferred to a separatory funnel the layers were separated The aqueous layer was added to ice the resulting recipitate was extracted with methylene chloride (5x) The combined extracts were washed with brine dried over magnesium sulfate filtered through a silica plug Solvents were removed under vacuum
Source ID: ord-7fb093c973b14a2f85e16d8a9352a423Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-102a2dd5872c403599c432ee23609084Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (411 mg, 2.3 mmol) (Step A) dissolved in a mixture of 7.9 mL of dry methylene chloride and 1.0 mL of dry tetrahydrofuran was treated with 1.62 mL (1.18 g, 11.6 mmol, 5 eq) of triethylamine and the resulting solution cooled to -15° C. Iodotrimethylsilane (0.66 mL, 932 mg, 4.7 mmol, 2 eq) was added followed by 1.183 g of iodine (4.7 mmol, 2 eq) added in small portions over 5 minutes. The mixture was warmed to room temperature over 5 minutes at which time 15 mL of methylene chloride was added followed by 20 mL of 10% aqueous sodium sulfite. The layers were separated and the organic layer washed with 10% sodium sulfite (3×20 mL). The aqueous layer was further extracted with 20 mL of methylene chloride. The combined extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated to dryness under vacuum. The crude product was chromatographed on silica gel, eluting with methylene chloride/methanol (99:1) to afford 511 mg (1.68 mmol, 73%) of the product. 1H NMR (300 MHz, CDCl3): 2.70 (m,3H), 2.93 (m,1H), 4.62 (t,9 Hz,1H), 6.95 (m,3H), 7.86 (br s,1H). FAB-MS: calculated for C10H9FINO 305; found 306 (M+H,100%). added in small portions over 5 minutes was added The layers were separated the organic layer washed with 10% sodium sulfite (3×20 mL) The aqueous layer was further extracted with 20 mL of methylene chloride The combined extracts were washed with brine dried over magnesium sulfate filtered concentrated to dryness under vacuum The crude product was chromatographed on silica gel eluting with methylene chloride/methanol (99:1)
Source ID: ord-e9ab89a7affd4faab496a36dc49a283fConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium azide 1.1 g (16.92 mmol) was added to a mixture of 6.0 mL of chloroform and 1.1 mL of water at 0° C. Concentrated sulfuric acid (0.44 mL) was added dropwise and the mixture stirred at 0° C. for two hours then filtered. The chloroform layer containing hydrazoic acid was added to a solution of 1.3 g (7.92 mmol) of 6-fluoro-1-tetralone (prepared by the method of Allinger and Jones, J. Org. Chem., 27, 70-76 (1962)) in 4.8 mL of chloroform. Additional sulfuric acid (2.16 mL) was added dropwise with stirring while maintaining the temperature below 40° C. The mixture was stirred at 40° C. for two hours then at room temperature for 16 hours. The mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was added to ice; the resulting precipitate was extracted with methylene chloride (5×). The combined extracts were washed with brine, dried over magnesium sulfate and filtered through a silica plug. Solvents were removed under vacuum to afford 162 mg (0.92 mmol,11%) of the product. 1H NMR (300 MHz, CDCl3): 2.21 (m,2H), 2.32 (t,7 Hz,2H), 2.77 (t,7 Hz,2H), 6.93 (m,3H), 7.8 (br s,1H). FAB-MS: calculated for C10H10FNO 179; found 180 (M+H,100%). then filtered The chloroform layer containing hydrazoic acid prepared by the method of Allinger and Jones, J with stirring while maintaining the temperature below 40° C The mixture was stirred at 40° C. for two hours at room temperature for 16 hours The mixture was transferred to a separatory funnel the layers were separated The aqueous layer was added to ice the resulting precipitate was extracted with methylene chloride (5×) The combined extracts were washed with brine dried over magnesium sulfate filtered through a silica plug Solvents were removed under vacuum
Source ID: ord-3ca1defbac2d4f369ed4efc315d01e05Conditions: temp:-15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 7-fluoro-2,3,4,5-tetrahydro-1H-1-benzazepin-2-one (411 mg, 2.3 mmol) (Step A) dissolved in a mixture of 7.9 mL of dry methylene chloride and 1.0 mL of dry tetrahydrofuran was treated with 1.62 mL (1.18 g, 11.6 mmol, 5 eq) of triethylamine and the resulting solution cooled to -15° C. Iodotrimethylsilane (0.66 mL, 932 mg, 4.7 mmol, 2 eq) was added followed by 1.183 g of iodine (4.7 mmol, 2 eq) added in small portions over 5 minutes. The mixture was warmed to room temperature over 5 minutes at which time 15 mL of methylene chloride was added followed by 20 mL of 10% aqueous sodium sulfite. The layers were separated and the organic layer washed with 10% sodium sulfite (3×20 mL). The aqueous layer was further extracted with 20 mL of methylene chloride. The combined extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated to dryness under vacuum. The crude product was chromatographed on silica gel, eluting with methylene chloride/methanol (99:1) to afford 511 mg (1.68 mmol, 73%) of the product. 1H NMR (300MHz, CDCl3): 2.70 (m,3H), 2.93 (m,1H), 4.62 (t,9Hz,1H), 6.95 (m,3H), 7.86 (br s,1H). FAB-MS: calculated for C10H9FINO 305; found 306 (M+H,100%). added in small portions over 5 minutes was added The layers were separated the organic layer washed with 10% sodium sulfite (3×20 mL) The aqueous layer was further extracted with 20 mL of methylene chloride The combined extracts were washed with brine dried over magnesium sulfate filtered concentrated to dryness under vacuum The crude product was chromatographed on silica gel eluting with methylene chloride/methanol (99:1)
Source ID: ord-8353b95d1e4943b1bf124f59cd32115aConditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: Sodium azide 1.1 g (16.92 mmol) was added to a mixture of 6.0 mL of chloroform and 1.1 mL of water at 0° C. Concentrated sulfuric acid (0.44 mL) was added dropwise and the mixture stirred at 0° C. for two hours then filtered. The chloroform layer containing hydrazoic acid was added to a solution of 1.3 g (7.92 mmol) of 6-fluoro-1-tetralone (prepared by the method of Allinger and Jones, J. Org. Chem., 27, 70-76 (1962)) in 4.8 mL of chloroform. Additional sulfuric acid (2.16 mL) was added dropwise with stirring while maintaining the temperature below 40° C. The mixture was stirred at 40° C. for two hours then at room temperature for 16 hours. The mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was added to ice; the resulting recipitate was extracted with methylene chloride (5x). The combined extracts were washed with brine, dried over magnesium sulfate and filtered through a silica plug. Solvents were removed under vacuum to afford 162 mg (0.92 mmol, 11%) of the product. 1H NMR (300MHz, CDCl3): 2.21 (m,2H), 2.32 (t,7Hz,2H), 2.7 (t,7Hz,2H), 6.93 (m,3H), 7.8 (br s,1H). FAB-MS: calculated for C10H10FNO 179; found 180 (M+H,100%). then filtered The chloroform layer containing hydrazoic acid prepared by the method of Allinger and Jones, J with stirring while maintaining the temperature below 40° C The mixture was stirred at 40° C. for two hours at room temperature for 16 hours The mixture was transferred to a separatory funnel the layers were separated The aqueous layer was added to ice the resulting recipitate was extracted with methylene chloride (5x) The combined extracts were washed with brine dried over magnesium sulfate filtered through a silica plug Solvents were removed under vacuum
Source ID: ord-7fb093c973b14a2f85e16d8a9352a423Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-102a2dd5872c403599c432ee23609084PubChem References
These sources are listed in the compound's public database record.
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