Hydrogen Bromide → 3-(Bromomethyl)-1-ethylpyrrolidine

HRID 1577017Notes

Reaction equation

HRID 1577017 reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][CH:5]([CH2:8]O)[CH2:4]1)[CH3:2].[BrH:10].C(=O)([O-])[O-].[Na+].[Na+]>>[Br:10][CH2:8][CH:5]1[CH2:6][CH2:7][N:3]([CH2:1][CH3:2])[CH2:4]1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 10340Sodium CarbonateHCID 21702849(1-Ethylpyrrolidin-3-yl)methanol

Product 1

HCID 215104953-(Bromomethyl)-1-ethylpyrrolidine

Procedure

A mixture of 5.0 g. (0.0388 mol.) of N-ethyl-3-hydroxymethylpyrrolidine and 50 ml. of 48% hydrogen bromide was refluxed for 17 hours. The reaction mixture was cooled, made basic by addition of solid sodium carbonate and extracted twice with methylene chloride. The combined extracts were dried (MgSO4) and evaporated to dryness to give 3-bromomethyl-N-ethylpyrrolidine.

Workup

  1. additionA mixture of 5.0 g
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted twice with methylene chloride
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-46401e28484943168e6253f41315513d
Source dataset
uspto-grants-1976_09
Patent number
US03983245

Reaction notes

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