1-Bromo-3-chloropropane → HCID 21316379, compound

HRID 866305Notes

Reaction equation

HRID 866305 reaction equation
[Br-:1].[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>[BrH:11].[Br-:1].[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 21316379HCID 21316379, compound

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-02ca4d77ac5646c9a09dc3f0052530f1
Source dataset
uspto-grants-1978_07
Patent number
US04098726

Reaction notes

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