Methanol → [2-(2-Chloro-4-nitro-phenyl)-ethyl]-(4-fluoro-benzyl)-amine

HRID 1019733Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH:12]=O.[F:14][C:15]1[CH:22]=[CH:21][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=1.CO.[BH4-].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][CH2:12][NH:20][CH2:19][C:18]1[CH:21]=[CH:22][C:15]([F:14])=[CH:16][CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2-(2-Chloro 4-nitro-phenyl)acetaldehyde (3.0 g, 15.03 mmol) and 4-fluorobenzylamine (1.88 g, 15.02 mmol) were added to methanol (45 mL) at RT and stirred for 15 minutes. The reaction mixture was cooled to 0° C. and acetic acid (15 mL) followed by solid NaBH4 (0.56 g, 15.0 mmol) were added. The reaction mixture was allowed to warm to RT and stirring continued for 2 hours. The volatiles were then removed under reduced pressure. Dichloromethane (60 mL) and water (60 mL) were added and the mixture was stirred for 15 minutes. The separated organic layer was washed with water (60 mL), brine (60 mL), dried (Na2SO4) and the solvents removed under reduced pressure to afford the title compound (3.1 g, 67%) which was used in the next step without further purification.

Workup

additionwere added
temperatureto warm to RT
stirringstirring
waitcontinued for 2 hours
customThe volatiles were then removed under reduced pressure
additionDichloromethane (60 mL) and water (60 mL) were added
stirringthe mixture was stirred for 15 minutes
washThe separated organic layer was washed with water (60 mL), brine (60 mL)
dry with materialdried (Na2SO4)
customthe solvents removed under reduced pressure

Sources & evidence

ORD record: ord-1148dd2c8b0e477dabb21c8d316d3515
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716287B2

Reaction notes

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