Chloride → 3-[N-(3-chloropropyl)methylamino]-N,N,N-trimethyl-propan-1-aminium chloride hydrochloride

HRID 328179Notes

Reaction equation

HRID 328179 reaction equation
[Br-].O[CH2:3][CH2:4][CH2:5][N:6]([CH2:8][CH2:9][CH2:10][N+:11]([CH3:14])([CH3:13])[CH3:12])[CH3:7].[ClH:15].[Cl-]>O>[ClH:15].[Cl-:15].[Cl:15][CH2:3][CH2:4][CH2:5][N:6]([CH2:8][CH2:9][CH2:10][N+:11]([CH3:14])([CH3:13])[CH3:12])[CH3:7]

Participants

5

Reactant 3

HCID 312ChlorideHCID 313Hydrochloric AcidHCID 233475683-[N'-(3-Hydroxypropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium Bromide2×

Product 1

HCID 233475703-[N-(3-chloropropyl)methylamino]-N,N,N-trimethyl-propan-1-aminium chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of 44.4 g. of product from Step 3, 3-[N'-(3-hydroxypropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium bromide, is dissolved in 500 ml. of water and acidified to pH 2 with concentrated hydrochloric acid. The solution is passed through a column of Dowex 1-X2 chloride form ion exchange resin and the eluant is evaporated under reduced pressure. The residual viscous oil is dried in vacuo and treated with thionyl chloride (25 ml.) added dropwise with stirring during one hour. The solution is heated at 50° for 1.5 hours and then evaporated under reduced pressure.

Workup

  1. customthe eluant is evaporated under reduced pressure
  2. customThe residual viscous oil is dried in vacuo
  3. additiontreated with thionyl chloride (25 ml.)
  4. additionadded dropwise
  5. temperatureThe solution is heated at 50° for 1.5 hours
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fd60219ef29f4bcda820c28cfa7e306d
Source dataset
uspto-grants-1977_04
Patent number
US04016209

Reaction notes

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