1,3-Dibromopropane → Didesmethylsibutramine

HRID 1188250Notes

Reaction equation

HRID 1188250 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.Br[CH2:12][CH2:13][CH2:14]Br>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2([CH:7]([NH2:8])[CH2:4][CH:5]([CH3:9])[CH3:6])[CH2:14][CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 80011,3-DibromopropaneHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 134772DidesmethylsibutramineYield 56.2%

Procedure

As described in article (Chinese Journal of Pharmaceuticals, 2001, 32(8): 337-339), p-chlorobenzyl cyanide was condensed with 1,3-dibromopropane, cycled to give cyclobutyl inter mediate, and then through Grignard reaction and reduction reaction to give title compound (56.2% yield).

Workup

  1. customto give cyclobutyl inter mediate
  2. customthrough Grignard reaction and reduction reaction

Sources & evidence

ORD record
ord-4c024b522e8d4ebf9564bd9c02bfb49a
Source dataset
uspto-grants-2014_03
Patent number
US08673981B2

Reaction notes

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