Sodium Hydroxide → 2-(4-Bromobenzyl)-1-methylpyrrolidine

HRID 1278056Notes

Reaction equation

HRID 1278056 reaction equation
[Br:1]Br.[CH2:3]([CH:10]1[CH2:14][CH2:13][CH2:12][N:11]1[CH3:15])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+]>[Fe]>[Br:1][C:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:15])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 10261602benzyl methylpyrrolidine

Product 1

HCID 234525932-(4-Bromobenzyl)-1-methylpyrrolidine

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

Add 11.4 moles of bromine at room temperature to 2 g of 2-benzyl-1-methylpyrrolidine and 50 mg of iron powder. Allow the resulting mixture to stand for 2 hours before rendering it alkaline 1 N sodium hydroxide solution. Extract the base with diethyl ether. Distil the ether extract to obtain the title compound as almost-colorless liquid of b.p. 72° at 0.001 mm of Hg.

Workup

  1. extractionExtract the base with diethyl ether
  2. customDistil the ether
  3. extractionextract

Sources & evidence

ORD record
ord-ae3e686b01884283883d52e184233057
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

Loading…