1-Bromo-3-chloropropane → 1-(3-Chloropropyl)-pyrrolidine

HRID 272811Notes

Reaction equation

HRID 272811 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].Br[CH2:9][CH2:10][CH2:11][Cl:12]>CC(C)=O>[Cl:12][CH2:11][CH2:10][CH2:9][N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 31268Pyrrolidine

Product 1

HCID 113210281-(3-Chloropropyl)-pyrrolidineYield 57%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Pyrrolidine (10 g, 0.14 mol), acetone (28 ml), 5M NaOH solution (21 ml) and 1-bromo-3-chloropropane (24.4 g, 0.15 mol) were stirred together under N2 for 8 hours. The organic layer was separated and concentrated in vacuo. The crude product was purified by vacuum distillation (b.p. 90° C./30 mbar) to give the title compound (11.7 g, 57%) as a colourless oil.

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated in vacuo
  3. distillationThe crude product was purified by vacuum distillation (b.p. 90° C./30 mbar)

Sources & evidence

ORD record
ord-113c6d7d00094d75b5bd1dc9e40e35cc
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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