Phenethylamine, m-trifluoromethyl- → HCID 69342519, compound

HRID 855306Notes

Reaction equation

HRID 855306 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]1([CH3:37])[CH2:36][CH2:35]1)[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]1([CH3:37])[CH2:36][CH2:35]1)[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 860938233-Chloro-4-(1-methylcyclopropyl)-benzaldehyde

Product 1

HCID 69342519HCID 69342519, compoundYield 89%

Procedure

The title compound was synthesized in analogy to (4-cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine (described in example S53) using 3-chloro-4-(1-methylcyclopropyl)-benzaldehyde (86 mg, 0.44 mmol), 2-(3-trifluoromethylphenyl)-ethylamine (84 mg, 0.44 mmol) and sodium borohydride (25 mg, 0.66 mmol). The desired product (145 mg, 89%) was isolated without further purification as a colorless oil. MS (ISP) 368.3 (M+H)+.

Sources & evidence

ORD record
ord-f0efd25bde0a48b785a02f40c255bb90
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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