3,4-Dichlorophenethylamine → [2-(3,4-Dichloro-phenyl)-ethyl]-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-amine

HRID 855218Notes

Reaction equation

HRID 855218 reaction equation
[F:1][C:2]1([F:13])[O:6][C:5]2[CH:7]=[CH:8][C:9]([CH:11]=O)=[CH:10][C:4]=2[O:3]1.[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][CH2:23][NH2:24])[CH:18]=[CH:19][C:20]=1[Cl:21].[BH4-].[Na+]>>[Cl:14][C:15]1[CH:16]=[C:17]([CH2:22][CH2:23][NH:24][CH2:11][C:9]2[CH:8]=[CH:7][C:5]3[O:6][C:2]([F:13])([F:1])[O:3][C:4]=3[CH:10]=2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

4

Reactant 3

HCID 2179583,4-DichlorophenethylamineHCID 27369732,2-Difluoro-5-formylbenzodioxoleHCID 4311764Sodium borohydride

Product 1

HCID 69346662[2-(3,4-Dichloro-phenyl)-ethyl]-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-amine

Procedure

[2-(3,4-dichloro-phenyl)-ethyl]-(2,2-difluoro-benzo[1,3]dioxol-5-ylmethyl)-amine was synthesized in analogy to the above procedure using 100 mg of 2,2-difluoro-1,3-benzodioxole-5-carbaldehyde (0.54 mmol), 102 mg of 2-(3,4-dichloro-phenyl)-ethylamine (0.54 mmol) and 31 mg of sodium borohydride (0.81 mmol). The isolated colorless semisolid (98 mg, 51%) was used in the following step without further purification. MS (ISP) 360.0 (M+H)+.

Workup

  1. customThe isolated colorless semisolid (98 mg, 51%) was used in the following step without further purification

Sources & evidence

ORD record
ord-c364b3ec74fb4de09444724fdde68d5a
Source dataset
uspto-grants-2007_08
Patent number
US07259183B2

Reaction notes

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