Phenethylamine, m-trifluoromethyl- → [3-Chloro-4-(1-methoxy-1-methyl-ethyl)-benzyl]-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

HRID 855333Notes

Reaction equation

HRID 855333 reaction equation
C1(C2C=CC(C[NH:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][C:15](F)=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=3)=CC=2)CC1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[C:34]([O:37][CH3:38])([CH3:36])[CH3:35])[CH:29]=O.FC(F)(F)C1C=C(CCN)C=CC=1.[BH4-].[Na+]>>[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[C:34]([O:37][CH3:38])([CH3:36])[CH3:35])[CH2:29][NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:13]=1

Participants

5

Reactant 4

HCID 104223Phenethylamine, m-trifluoromethyl-HCID 4311764Sodium borohydrideHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amineHCID 86093855HCID 86093855, compound

Product 1

HCID 69342163[3-Chloro-4-(1-methoxy-1-methyl-ethyl)-benzyl]-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

Procedure

The title compound was synthesized in analogy to (4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine (described in example S53) using 77 mg of 3-chloro-4-(1-methoxy-1-methyl-ethyl)-benzaldehyde (0.36 mmol), 68 mg of 2-(3-trifluoromethylphenyl)-ethylamine (0.36 mmol) and 21 mg of sodium borohydride (0.54 mmol). The isolated colorless liquid (113 mg, 81%) was used in the following step without further purification. MS (ISP) 386.2 (M+H)+.

Workup

  1. customThe isolated colorless liquid (113 mg, 81%) was used in the following step without further purification

Sources & evidence

ORD record
ord-d93b6fb3d44248398547f5e03b379838
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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