Dimethylamine → (3-(Dimethylamino)propyl)triphenylphosphonium bromide hydrobromide

HRID 1196987Notes

Reaction equation

HRID 1196987 reaction equation
[BrH:1].[Br-].[Br:3][CH2:4][CH2:5][CH2:6][P+:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:26][NH:27][CH3:28]>C(O)C>[BrH:3].[Br-:1].[CH3:26][N:27]([CH3:28])[CH2:4][CH2:5][CH2:6][P+:7]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 19897085(3-Bromopropyl)-triphenylphosphonium bromide hydrobromide

Product 1

HCID 23651404(3-(Dimethylamino)propyl)triphenylphosphonium bromide hydrobromide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Then, 100.0 g of (3-bromopropyl)-triphenylphosphonium bromide hydrobromide is suspended in 500 ml of ethanol and 300 ml of 50% aqueous dimethylamine solution is added thereto. After heating the mixture at reflux for 10 minutes, the mixture is allowed to stand for cooling. The solvent is distilled away under reduced pressure and the resultant crude product is recrystallized from ethanol to obtain 64.0 g of the desired product having the physicochemical properties as identified in Table 8.

Workup

  1. temperatureAfter heating the mixture
  2. temperatureat reflux for 10 minutes
  3. temperaturefor cooling
  4. distillationThe solvent is distilled away under reduced pressure
  5. customthe resultant crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-a8437e3468174024ae8d418037873a05
Source dataset
uspto-grants-1992_05
Patent number
US05116863

Reaction notes

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