Phenethylamine, m-trifluoromethyl- → [4-(1,1-Dimethylpropyl)-benzyl]-[2-(3-trifluoromethylphenyl)-ethyl]-amine

HRID 855300Notes

Reaction equation

HRID 855300 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.[CH3:25][C:26]([C:30]1[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=1)([CH3:29])[CH2:27][CH3:28].FC(F)(F)C1C=C(CCN)C=CC=1.[BH4-].[Na+]>>[CH3:25][C:26]([C:30]1[CH:37]=[CH:36][C:33]([CH2:34][NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:13]=2)=[CH:32][CH:31]=1)([CH3:29])[CH2:27][CH3:28]

Participants

5

Reactant 4

HCID 104223Phenethylamine, m-trifluoromethyl-HCID 4737804-(2-Methylbutan-2-yl)benzaldehydeHCID 4311764Sodium borohydrideHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine

Product 1

HCID 69341945[4-(1,1-Dimethylpropyl)-benzyl]-[2-(3-trifluoromethylphenyl)-ethyl]-amineYield 94%

Procedure

The title compound was synthesized in analogy to (4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine (described in example S53) using 4-(1,1-dimethylpropyl)-benzaldehyde (prepared as described in example S103) (88 mg, 0.50 mmol), 2-(3-trifluoromethylphenyl)-ethylamine (94 mg, 0.50 mmol) and sodium borohydride (28 mg, 0.75 mmol). The desired product (163 mg, 94%) was isolated without further purification as a colorless oil. MS (ISP) 350.3 (M+H)+.

Sources & evidence

ORD record
ord-8531210324f84aca98814047268ec9b2
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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