3,4-Dichlorophenethylamine → (4-Cyclopentyl-benzyl)-[2-(3,4-dichloro-phenyl)-ethyl]-amine

HRID 855329Notes

Reaction equation

C1(C2C=CC(CNCCC3C=CC(F)=C(C(F)(F)F)C=3)=CC=2)CC1.[CH:25]1([C:30]2[CH:37]=[CH:36][C:33]([CH:34]=O)=[CH:32][CH:31]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1.[Cl:38][C:39]1[CH:40]=[C:41]([CH2:46][CH2:47][NH2:48])[CH:42]=[CH:43][C:44]=1[Cl:45].[BH4-].[Na+]>>[CH:25]1([C:30]2[CH:37]=[CH:36][C:33]([CH2:34][NH:48][CH2:47][CH2:46][C:41]3[CH:42]=[CH:43][C:44]([Cl:45])=[C:39]([Cl:38])[CH:40]=3)=[CH:32][CH:31]=2)[CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Reactant 4

HCID 2179583,4-Dichlorophenethylamine

HCID 3016187p-Cyclopentylbenzaldehyde

HCID 4311764Sodium borohydride

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

Product 1

HCID 69342726(4-Cyclopentyl-benzyl)-[2-(3,4-dichloro-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 160 mg of 4-cyclopentyl-benzaldehyde (0.92 mmol), 175 mg of 2-(3,4-dichloro-phenyl)-ethylamine (0.92 mmol) and 52 mg of sodium borohydride (1.38 mmol). The isolated light yellow oil (183 mg, 57%) was used in the following step without further purification. MS (ISP) 348.2 (M+H)+.

Workup

customThe isolated light yellow oil (183 mg, 57%) was used in the following step without further purification

Sources & evidence

ORD record: ord-807d72f3e1724f80ab383e4721d7037b
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259183B2

Reaction notes

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