No renderable structure data available
CN(C)C(=O)CCCCClChemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 5-chloro-N,N-dimethylpentanamide |
|---|---|
| IUPAC Name | — |
| CAS Number | 53101-21-6 |
| Database ID | 11252183 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
5-chloro-N,N-dimethylpentanamide (CAS 53101-21-6) 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 11252183
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
9 reactions · 9 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-b6865d465336424a987e01ad44e96a35Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 7.0 g (0.023 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.8 g (0.028 mole) of 5-chloro-N,N-dimethylpentanamide, 9.8 g (0.092 mole) of anhydrous sodium carbonate and 0.3 g (0.008 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 1.5 L of water and extracted twice with 200 ml portions of ethyl acetate. The ethyl acetate fractions were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a viscous oil. The oil was purified by column chromatography using 250 g of silica gel on a 69 cm×4 cm column, eluted with 10% methanol in methylene chloride. The fractions containing the desired product were combined and concentrated under reduced pressure to give a viscous oil. The oil was converted to the oxalic acid salt and the solid was recrystallized from 2-propanol to yield 6.2 g (52%) of white solid, mp 193°-195° C. was heated on a steam bath for 16 h extracted twice with 200 ml portions of ethyl acetate washed with water and brine dried (MgSO4) concentrated under reduced pressure to give a viscous oil The oil was purified by column chromatography eluted with 10% methanol in methylene chloride The fractions containing the desired product concentrated under reduced pressure to give a viscous oil the solid was recrystallized from 2-propanol
Source ID: ord-e733fd7e260a47dca66d3c8a451ce6f9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 20.0 g (0.44 mole) of dimethylamine in 100 ml of cold tetrahydrofuran (THF) was added dropwise to a solution of 20.0 g (0.13 mole) of 5-chlorovaleryl chloride in 100 ml of THF. The reaction mixture was stirred mechanically and the temperature maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove solid precipitates, and the filtrate was concentrated under reduced pressure to yield 18.0 g (85%) of yellow oil. An analytical sample was prepared by filtering this oil through a small bed of silica gel and eluting with ethyl acetate-hexane (1:1). The fractions containing the desired product were combined and concentrated under reduced pressure to give the title compound as a light-yellow oil. the temperature maintained between 5° and 15° C. throughout the addition After the final addition the solution was filtered to remove solid precipitates the filtrate was concentrated under reduced pressure
Source ID: ord-8f1e7ecea9dd46bbbdfc372fc1cbdd94Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 7.0 g (0.023 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.8 g (0.028 mole) of 5-chloro-N,N-dimethylpentanamide, 9.8 g (0.092 mole) of anhydrous sodium carbonate and 0.3 g (0.008 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 1.5 L of water and extracted twice with 200 ml portions of ethyl acetate. The ethyl acetate fractions were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a viscous oil. The oil was purified by column chromatography using 250 g of silica gel on a 69 cm×4 cm column, eluted with 10% methanol in methylene chloride. The fractions containing the desired product were combined and concentrated under reduced pressure to give a viscous oil. The oil was converted to the oxalic acid salt and the solid was recrystallized from 2-propanol to yield 6.2 g (52%) of white solid, mp 193°-195° C. was heated on a steam bath for 16 h extracted twice with 200 ml portions of ethyl acetate washed with water and brine dried (MgSO4) concentrated under reduced pressure to give a viscous oil The oil was purified by column chromatography eluted with 10% methanol in methylene chloride The fractions containing the desired product concentrated under reduced pressure to give a viscous oil the solid was recrystallized from 2-propanol
Source ID: ord-e733fd7e260a47dca66d3c8a451ce6f9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 7.0 g (0.023 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.8 g (0.028 mole) of 5-chloro-N,N-dimethylpentanamide, 9.8 g (0.092 mole) of anhydrous sodium carbonate and 0.3 g (0.008 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 1.5 L of water and extracted twice with 200 ml portions of ethyl acetate. The ethyl acetate fractions were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a viscous oil. The oil was purified by column chromatography using 250 g of silica gel on a 69 cm×4 cm column, eluted with 10% methanol in methylene chloride. The fractions containing the desired product were combined and concentrated under reduced pressure to give a viscous oil. The oil was converted to the oxalic acid salt and the solid was recrystallized from 2-propanol to yield 6.2 g (52%) of white solid, mp 193°-195° C. was heated on a steam bath for 16 h extracted twice with 200 ml portions of ethyl acetate washed with water and brine dried (MgSO4) concentrated under reduced pressure to give a viscous oil The oil was purified by column chromatography eluted with 10% methanol in methylene chloride The fractions containing the desired product concentrated under reduced pressure to give a viscous oil the solid was recrystallized from 2-propanol
Source ID: ord-e733fd7e260a47dca66d3c8a451ce6f9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 20.0 g (0.44 mole) of dimethylamine in 100 ml of cold tetrahydrofuran (THF) was added dropwise to a solution of 20.0 g (0.13 mole) of 5-chlorovaleryl chloride in 100 ml of THF. The reaction mixture was stirred mechanically and the temperature maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove solid precipitates, and the filtrate was concentrated under reduced pressure to yield 18.0 g (85%) of yellow oil. An analytical sample was prepared by filtering this oil through a small bed of silica gel and eluting with ethyl acetate-hexane (1:1). The fractions containing the desired product were combined and concentrated under reduced pressure to give the title compound as a light-yellow oil. the temperature maintained between 5° and 15° C. throughout the addition After the final addition the solution was filtered to remove solid precipitates the filtrate was concentrated under reduced pressure
Source ID: ord-8f1e7ecea9dd46bbbdfc372fc1cbdd94Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 20.0 g (0.44 mole) of dimethylamine in 100 ml of cold tetrahydrofuran (THF) was added dropwise to a solution of 20.0 g (0.13 mole) of 5-chlorovaleryl chloride in 100 ml of THF. The reaction mixture was stirred mechanically and the temperature maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove solid precipitates, and the filtrate was concentrated under reduced pressure to yield 18.0 g (85%) of yellow oil. An analytical sample was prepared by filtering this oil through a small bed of silica gel and eluting with ethyl acetate-hexane (1:1). The fractions containing the desired product were combined and concentrated under reduced pressure to give the title compound as a light-yellow oil. the temperature maintained between 5° and 15° C. throughout the addition After the final addition the solution was filtered to remove solid precipitates the filtrate was concentrated under reduced pressure
Source ID: ord-8f1e7ecea9dd46bbbdfc372fc1cbdd94Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A mixture of 7.0 g (0.023 mole) of α,α-bis(4-fluorophenyl)-4-piperidinemethanol, 4.8 g (0.028 mole) of 5-chloro-N,N-dimethylpentanamide, 9.8 g (0.092 mole) of anhydrous sodium carbonate and 0.3 g (0.008 mole) of potassium iodide in 100 ml of N,N-dimethylformamide was heated on a steam bath for 16 h. The mixture was poured into 1.5 L of water and extracted twice with 200 ml portions of ethyl acetate. The ethyl acetate fractions were combined, washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give a viscous oil. The oil was purified by column chromatography using 250 g of silica gel on a 69 cm×4 cm column, eluted with 10% methanol in methylene chloride. The fractions containing the desired product were combined and concentrated under reduced pressure to give a viscous oil. The oil was converted to the oxalic acid salt and the solid was recrystallized from 2-propanol to yield 6.2 g (52%) of white solid, mp 193°-195° C. was heated on a steam bath for 16 h extracted twice with 200 ml portions of ethyl acetate washed with water and brine dried (MgSO4) concentrated under reduced pressure to give a viscous oil The oil was purified by column chromatography eluted with 10% methanol in methylene chloride The fractions containing the desired product concentrated under reduced pressure to give a viscous oil the solid was recrystallized from 2-propanol
Source ID: ord-e733fd7e260a47dca66d3c8a451ce6f9Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: A solution of 20.0 g (0.44 mole) of dimethylamine in 100 ml of cold tetrahydrofuran (THF) was added dropwise to a solution of 20.0 g (0.13 mole) of 5-chlorovaleryl chloride in 100 ml of THF. The reaction mixture was stirred mechanically and the temperature maintained between 5° and 15° C. throughout the addition. After the final addition, the solution was filtered to remove solid precipitates, and the filtrate was concentrated under reduced pressure to yield 18.0 g (85%) of yellow oil. An analytical sample was prepared by filtering this oil through a small bed of silica gel and eluting with ethyl acetate-hexane (1:1). The fractions containing the desired product were combined and concentrated under reduced pressure to give the title compound as a light-yellow oil. the temperature maintained between 5° and 15° C. throughout the addition After the final addition the solution was filtered to remove solid precipitates the filtrate was concentrated under reduced pressure
Source ID: ord-8f1e7ecea9dd46bbbdfc372fc1cbdd94PubChem References
These sources are listed in the compound's public database record.
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