Phenethylamine, m-trifluoromethyl- → (4-Cyclobutyl-benzyl)-[2-(3-trifluoromethyl-phenyl)-ethyl]-amine

HRID 855325Notes

Reaction equation

HRID 855325 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.[CH:25]1(C2C=CC(C=O)=CC=2)CCC1.FC(F)(F)C1C=C(CCN)C=CC=1.[BH4-].[Na+]>>[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([CH2:8][NH:9][CH2:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:19]([F:20])([F:22])[F:21])[CH:13]=3)=[CH:23][CH:24]=2)[CH2:3][CH2:2][CH2:25]1

Participants

5

Reactant 4

HCID 104223Phenethylamine, m-trifluoromethyl-HCID 4311764Sodium borohydrideHCID 571743534-CyclobutylbenzaldehydeHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine

Product 1

HCID 68697814(4-Cyclobutyl-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 180 mg of 4-cyclobutyl-benzaldehyde (1.23 mmol) (described in example S113), 213 mg of 2-(3-trifluoromethylphenyl)-ethylamine (1.23 mmol) and 64 mg of sodium borohydride (1.69 mmol). The isolated yellow oil (343 mg, 92%) was used in the following step without further purification. 1H NMR (CDCl3, 300 MHz): δ 1.85 (m, 1H), 1.92-2.21 (m, 3H), 2.33 (m, 2H), 2.89 (m, 4H), 3.53 (quint, J=9 Hz, 1H), 3.78 (s, 2H), 7.19 (m, 4H), 7.39 (m, 2H), 7.46 (m, 2H).

Workup

  1. customThe isolated yellow oil (343 mg, 92%) was used in the following step without further purification

Sources & evidence

ORD record
ord-05bbf3d7e952448bac5dd780e1fb4bd9
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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