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

HRID 855271Notes

Reaction equation

[CH:1]1([C:4]2[CH:24]=[CH:23][C:7]([CH2:8][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)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.[CH3:25]C1(C2C=CC(C=O)=CC=2)CC1.FC(F)(F)C1C=C(CCN)C=CC=1.[BH4-].[Na+]>>[CH3:25][C:1]1([C:4]2[CH:24]=[CH:23][C:7]([CH2:8][NH:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

Reactant 4

HCID 104223Phenethylamine, m-trifluoromethyl-

HCID 4311764Sodium borohydride

HCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine

HCID 860938474-(1-Methylcyclopropyl)benzaldehyde

Product 1

HCID 69342738[4-(1-Methylcyclopropyl)-benzyl]-[2-(3-trifluoromethylphenyl)-ethyl]-amineYield 62%

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-methyl-cyclo-propyl)-benzaldehyde (150 mg, 0.94 mmol), 2-(3-trifluoromethylphenyl)-ethylamine (177 mg, 0.94 mmol) and sodium borohydride (53 mg, 1.40 mmol). The isolated residue was purified by flash column chromatography (2%-5% MeOH in EtOAc) to give the desired product (195 mg, 62%) as a colorless oil. MS (ISP) 334.3 (M+H)+.

Workup

customThe isolated residue was purified by flash column chromatography (2%-5% MeOH in EtOAc)

Sources & evidence

ORD record: ord-68755597b46146b0a46321230ff37374
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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