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

HRID 855290

Reaction equation

HRID 855290 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][O:26][C:27]1([C:31]2[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=2)[CH2:30][CH2:29][CH2:28]1.FC(F)(F)C1C=C(CCN)C=CC=1.[BH4-].[Na+]>>[CH3:25][O:26][C:27]1([C:31]2[CH:38]=[CH:37][C:34]([CH2:35][NH:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([F:20])([F:21])[F:22])[CH:13]=3)=[CH:33][CH:32]=2)[CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 4

HCID 104223Phenethylamine, m-trifluoromethyl-HCID 4311764Sodium borohydrideHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amineHCID 860937504-(1-Methoxycyclobutyl)benzaldehyde

Product 1

HCID 69343056[4-(1-Methoxycyclobutyl)-benzyl]-[2-(3-trifluoromethylphenyl)-ethyl]-amineYield 77%

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-methoxycyclobutyl)-benzaldehyde (76 mg, 0.40 mmol), 2-(3-trifluoromethylphenyl)-ethylamine (76 mg, 0.40 mmol) and sodium borohydride (17 mg, 0.44 mmol). The isolated residue was purified by flash column chromatography (2%-5% MeOH in EtOAc) to give the desired product (112 mg, 77%) as a colorless oil. MS (ISP) 364.3 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-193dc1616d2149f99190b69de16f80ce
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Linked notes

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