N-benzylformamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 690 mg (5.1 mmoles) of N-benzylformamide in 5 ml of methylene chloride is cooled in an ice-water bath and put under an argon blanket. The solution is stirred while 4.9 ml (4.9 mmoles) of 1 M triethyloxonium fluoroborate in methylene chloride is added dropwise. After a 45 minute reaction time, the mixture is concentrated to dryness under reduced pressure at room temperature, and the residue is dried under reduced pressure over P2O5. The nuclear magnetic resonance spectrum of the product in deuterochloroform is fully in accord with the product being a fluoroborate etherate complex of ethyl N-benzylformimidate. is added dropwise After a 45 minute reaction time the mixture is concentrated to dryness under reduced pressure at room temperature the residue is dried under reduced pressure over P2O5

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using general procedure A, N-benzylformamide (170 mg, 1.26 mmol) was coupled with 5-iodo-m-xylene (150 μL, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×5 cm; hexane-ethyl acetate 3:1; 15 mL fractions). Fractions 7-13 provided 247 mg (99% yield) of the product as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 8.55 (s, 1H), 7.39-7.22 (m, 5H), 6.91 (s, 1H), 6.75 (s, 2H), 5.00 (s, 2H), 2.30 (s, 6H). The crude product was purified by flash chromatography on silica gel (2×5 cm; hexane-ethyl acetate 3:1; 15 mL fractions)

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a round-bottom flask, 9.9 g of purified N-benzyl formamide and 4 g of NaSCN (sodium thiocyanate) were introduced. The mixture was agitated gradually under nitrogen atmosphere at 30° C. for 40 minutes, and then at room temperature for 5 hours to obtain 10.7 g of N-benzyl formamide-NaSCN eutectic mixture.

Conditions: temp:30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a round-bottom flask, 9.9 g of purified N-benzyl formamide and 4 g of NaSCN (sodium thiocyanate) were introduced. The mixture was agitated gradually under nitrogen atmosphere at 30° C. for 40 minutes, and then at room temperature for 5 hours to obtain 10.7 g of N-benzyl formamide-NaSCN eutectic mixture.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 690 mg (5.1 mmoles) of N-benzylformamide in 5 ml of methylene chloride is cooled in an ice-water bath and put under an argon blanket. The solution is stirred while 4.9 ml (4.9 mmoles) of 1 M triethyloxonium fluoroborate in methylene chloride is added dropwise. After a 45 minute reaction time, the mixture is concentrated to dryness under reduced pressure at room temperature, and the residue is dried under reduced pressure over P2O5. The nuclear magnetic resonance spectrum of the product in deuterochloroform is fully in accord with the product being a fluoroborate etherate complex of ethyl N-benzylformimidate. is added dropwise After a 45 minute reaction time the mixture is concentrated to dryness under reduced pressure at room temperature the residue is dried under reduced pressure over P2O5

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 690 mg (5.1 mmoles) of N-benzylformamide in 5 ml of methylene chloride is cooled in an ice-water bath and put under an argon blanket. The solution is stirred while 4.9 ml (4.9 mmoles) of 1 M triethyloxonium fluoroborate in methylene chloride is added dropwise. After a 45 minute reaction time, the mixture is concentrated to dryness under reduced pressure at room temperature, and the residue is dried under reduced pressure over P2O5. The nuclear magnetic resonance spectrum of the product in deuterochloroform is fully in accord with the product being a fluoroborate etherate complex of ethyl N-benzylformimidate. is added dropwise After a 45 minute reaction time the mixture is concentrated to dryness under reduced pressure at room temperature the residue is dried under reduced pressure over P2O5

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using procedure 41, methyl 2-(dipropylamino)-6-ethoxy-2,3-dihydro-1H-indene-5-carboxylate (77, 0.32 g, 1 mmol) was treated with N-benzylformamide (1.35 g, 10 mmol). Chromatographic purification yielded pure product 84 as a oil which was converted into the HCl salt and crystallized from EtOAc to give a white solid (m.p. 219-221° C.). Chromatographic purification

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Using general procedure A, N-benzylformamide (170 mg, 1.26 mmol) was coupled with 5-iodo-m-xylene (150 μL, 1.04 mmol). The crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 3:1; 15 mL fractions). Fractions 7-13 provided 247 mg (99% yield) of the product as a colorless oil. 1H NMR (400 MHz, CDCl3): δ 8.55 (s, 1H), 7.39-7.22 (m, 5H), 6.91 (s, 1H), 6.75 (s, 2H), 5.00 (s, 2H), 2.30 (s, 6H). The crude product was purified by flash chromatography on silica gel (2×15 cm; hexane-ethyl acetate 3:1; 15 mL fractions)