3,4-Dichlorophenethylamine → [3-Chloro-4-(1-methoxy-1-methyl-ethyl)-benzyl]-[2-(3,4-dichloro-phenyl)-ethyl]-amine

HRID 855334Notes

Reaction equation

HRID 855334 reaction equation
C1(C2C=CC(CNCCC3C=CC(F)=C(C(F)(F)F)C=3)=CC=2)CC1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[C:34]([O:37][CH3:38])([CH3:36])[CH3:35])[CH:29]=O.[Cl:39][C:40]1[CH:41]=[C:42]([CH2:47][CH2:48][NH2:49])[CH:43]=[CH:44][C:45]=1[Cl:46].[BH4-].[Na+]>>[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[C:34]([O:37][CH3:38])([CH3:36])[CH3:35])[CH2:29][NH:49][CH2:48][CH2:47][C:42]1[CH:43]=[CH:44][C:45]([Cl:46])=[C:40]([Cl:39])[CH:41]=1

Participants

5

Reactant 4

HCID 2179583,4-DichlorophenethylamineHCID 4311764Sodium borohydrideHCID 69342889(4-Cyclopropylbenzyl)-[2-(4-fluoro-3-trifluoromethylphenyl)-ethyl]-amineHCID 86093855HCID 86093855, compound

Product 1

HCID 69343168[3-Chloro-4-(1-methoxy-1-methyl-ethyl)-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 77 mg of 3-chloro-4-(1-methoxy-1-methyl-ethyl)-benzaldehyde (0.36 mmol) (described in example S117), 69 mg of 2-(3,4-dichloro-phenyl)-ethylamine (0.36 mmol) and 21 mg of sodium borohydride (0.54 mmol). The isolated colorless liquid (126 mg, 90%) was used in the following step without further purification. MS (ISP) 386.1 (M+H)+.

Workup

  1. customThe isolated colorless liquid (126 mg, 90%) was used in the following step without further purification

Sources & evidence

ORD record
ord-f986c86531c3455886a78c0096fe1506
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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