N,N-Dimethylbenzylamine → N-Benzyl-N,N-dimethyl-2-phenoxyethan-1-aminium bromide

HRID 893554Notes

Reaction equation

HRID 893554 reaction equation
[C:1]1([O:7][CH2:8][CH2:9][Br:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:11][N:12]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH3:13]>C(#N)C>[Br-:10].[CH3:11][N+:12]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:13])[CH2:9][CH2:8][O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7681N,N-DimethylbenzylamineHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 23176407N-Benzyl-N,N-dimethyl-2-phenoxyethan-1-aminium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 40.21 grams (0.20 mol) of 2-bromoethyl phenyl ether, 27.04 grams (0.20 mol) of N,N-dimethylbenzylamine and 135 milliters of acetonitrile was heated at reflux for 16.75 hrs. The reaction mixture was concentrated and then cooled. On standing, the residue crystallized. The solid was stirred in ether, collected and dried. The yield of product was 66.0 grams (98.13% of theory); mp=100°-110° C.

Workup

  1. temperatureat reflux for 16.75 hrs
  2. concentrationThe reaction mixture was concentrated
  3. temperaturecooled
  4. customthe residue crystallized
  5. customcollected
  6. customdried

Sources & evidence

ORD record
ord-65467509b4c04762abd9bb97304c1ed0
Source dataset
uspto-grants-1992_06
Patent number
US05126225

Reaction notes

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