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

HRID 855324Notes

Reaction equation

HRID 855324 reaction equation
C1(C2C=CC(CNCCC3C=CC(F)=C(C(F)(F)F)C=3)=CC=2)CC1.[CH:25]1([C:29]2[CH:36]=[CH:35][C:32]([CH:33]=O)=[CH:31][CH:30]=2)[CH2:28][CH2:27][CH2:26]1.[Cl:37][C:38]1[CH:39]=[C:40]([CH2:45][CH2:46][NH2:47])[CH:41]=[CH:42][C:43]=1[Cl:44].[BH4-].[Na+]>>[CH:25]1([C:29]2[CH:36]=[CH:35][C:32]([CH2:33][NH:47][CH2:46][CH2:45][C:40]3[CH:41]=[CH:42][C:43]([Cl:44])=[C:38]([Cl:37])[CH:39]=3)=[CH:31][CH:30]=2)[CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 4

HCID 2179583,4-DichlorophenethylamineHCID 4311764Sodium borohydrideHCID 571743534-CyclobutylbenzaldehydeHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amine

Product 1

HCID 68699197(4-Cyclobutyl-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 200 mg of 4-cyclobutyl-benzaldehyde (1.25 mmol), 237 mg of 2-(3,4-dichloro-phenyl)-ethylamine (1.25 mmol) and 71 mg of sodium borohydride (1.87 mmol). The isolated yellow oil (416 mg, 100%) was used in the following step without further purification. 1H NMR (CDCl3, 300 MHz): δ 1.84 (m, 1H), 1.95-2.21 (m, 3H), 2.33 (m, 2H), 2.76 (m, 2H), 2.87 (m, 2H), 3.53 (quint, J=9 Hz, 1H), 3.76 (s, 2H), 7.03 (dd, J=8 and 2 Hz, 1H), 7.19 (m, 4H), 7.29 (d, J=2 Hz, 1H), 7.34 (d, J=8 Hz, 1H).

Workup

  1. customThe isolated yellow oil (416 mg, 100%) was used in the following step without further purification

Sources & evidence

ORD record
ord-a4788a58e6664ad49df4d310d5348637
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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