1-Bromo-3-chloropropane → 3-[N'-(3-Chloropropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium Bromide

HRID 263169Notes

Reaction equation

HRID 263169 reaction equation
[Br-].[CH3:2][N+:3]([CH3:10])([CH3:9])[CH2:4][CH2:5][CH2:6][NH:7][CH3:8].[Br:11][CH2:12][CH2:13][CH2:14][Cl:15]>C(#N)C>[Br-:11].[Cl:15][CH2:14][CH2:13][CH2:12][N:7]([CH2:6][CH2:5][CH2:4][N+:3]([CH3:10])([CH3:9])[CH3:2])[CH3:8]

Participants

4

Reactant 2

HCID 80061-Bromo-3-chloropropaneHCID 21444211N,N,N-Trimethyl-3-(methylamino)propan-1-aminium bromide

Product 1

HCID 213163783-[N'-(3-Chloropropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium Bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of 3.02 g. (14.3 mmoles) of N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide in 30 ml. of acetonitrile is added a solution of 2.25 g. (14.3 mmoles) of 3-bromo-1-chloropropane and the mixture is stirred at room temperature under nitrogen for 3.5 hours. The mixture is cooled in an ice-water bath and then the insoluble material is removed by filtration. The filtrate is evaporated and dried in vacuo and is extracted with chloroform. The chloroform extract is evaporated and dried to give 2.05 g. (100%) of oily product; NMR δ: 2.2 (3H, S, --NCH3); 3.43 (9H, S, --N+ (CH3)3).

Workup

  1. temperatureThe mixture is cooled in an ice-water bath
  2. customthe insoluble material is removed by filtration
  3. customThe filtrate is evaporated
  4. customdried in vacuo
  5. extractionis extracted with chloroform
  6. extractionThe chloroform extract
  7. customis evaporated
  8. customdried
  9. customto give 2.05 g

Sources & evidence

ORD record
ord-1f60abf9c5b0446b8b37346274887e16
Source dataset
uspto-grants-1979_05
Patent number
US04156693

Reaction notes

Loading…