3,4-Dimethylpyridine → 1-[[3-[Acetyl[[4-(tetradecyloxy)phenyl]methyl]amino]phenyl]methyl]-3,4-dimethylpyridinium bromide

HRID 483584

Reaction equation

HRID 483584 reaction equation
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:16][CH:15]=2)[C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.[N:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([CH3:42])[CH:36]=1>C(#N)C>[Br-:1].[C:10]([N:9]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])=[CH:16][CH:15]=1)[C:5]1[CH:4]=[C:3]([CH2:2][N+:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([CH3:42])[CH:36]=2)[CH:8]=[CH:7][CH:6]=1)(=[O:12])[CH3:11]

Participants

4

Reactant 2

HCID 114173,4-DimethylpyridineHCID 10414650N-[3-(bromomethyl)phenyl]-N-[[4-(tetradecyloxy)phenyl]methyl]acetamide

Product 1

HCID 150301401-[[3-[Acetyl[[4-(tetradecyloxy)phenyl]methyl]amino]phenyl]methyl]-3,4-dimethylpyridinium bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1.6 g of N-[3-(bromomethyl)phenyl]-N-[[4-(tetradecyloxy)phenyl]methyl]acetamide and 1.29 g of 3,4-lutidine in 25 ml of acetonitrile is refluxed under argon for 5 hours. The solvent is evaporated and the residue stirred with ether. The solid is collected by centrifugation, washed several times with ether and vacuum dried to give the desired product as a solid, m.p. 100°-103° C.

Workup

  1. temperatureis refluxed under argon for 5 hours
  2. customThe solvent is evaporated
  3. customThe solid is collected by centrifugation
  4. washwashed several times with ether and vacuum
  5. customdried

Sources & evidence

ORD record
ord-3baf85850f45437986d5b6dc2e9f6ab1
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Linked notes

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