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

HRID 328181Notes

Reaction equation

HRID 328181 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-ba4e659c683d406994a8b1c9d2b5d8ed
Source dataset
uspto-grants-1977_04
Patent number
US04016209

Reaction notes

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