Benzyl Chloride → N,N-Dimethyl-N-(2-benzoylaminoethyl)benzylammonium Chloride

HRID 372939

Reaction equation

HRID 372939 reaction equation
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[Cl:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(#N)C>[Cl-:15].[CH3:1][N+:2]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([CH3:14])[CH2:3][CH2:4][NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 113158N-(2-(Dimethylamino)ethyl)benzamide

Product 1

HCID 19811098N,N-Dimethyl-N-(2-benzoylaminoethyl)benzylammonium Chloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 19.23 grams (0.10 mol) of the N-(2-dimethylaminoethyl)benzamide, prepared as described in Example 1, 12.66 grams (0.10 mol) of α-chlorotoluene and 64 milliters of acetonitrile was heated at reflux for 19.75 hours. Solid crystallized on cooling which was collected, washed with acetonitrile and dried. The yield of product was 24.0 grams (75.27% of theory); mp=175°-176° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 19.75 hours
  3. customSolid crystallized
  4. temperatureon cooling which
  5. customwas collected
  6. washwashed with acetonitrile
  7. customdried

Sources & evidence

ORD record
ord-80630acfb6e64d19be126317e4c1d130
Source dataset
uspto-grants-1992_11
Patent number
US05162188

Linked notes

Loading…