1,3-Diiodopropane → 3-[N'-(3-Iodopropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium Iodide

HRID 866306Notes

Reaction equation

HRID 866306 reaction equation
[Br-].[CH3:2][N+:3]([CH3:10])([CH3:9])[CH2:4][CH2:5][CH2:6][NH:7][CH3:8].[I:11][CH2:12][CH2:13][CH2:14]I>C(#N)C>[I-:11].[I:11][CH2:12][CH2:13][CH2:14][N:7]([CH2:6][CH2:5][CH2:4][N+:3]([CH3:10])([CH3:9])[CH3:2])[CH3:8]

Participants

4

Reactant 2

HCID 123141,3-DiiodopropaneHCID 21444211N,N,N-Trimethyl-3-(methylamino)propan-1-aminium bromide

Product 1

HCID 213163643-[N'-(3-Iodopropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium Iodide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of 216.2 mg. (1 mmole) of N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide in 1.5 ml. of acetonitrile is added a solution of 296 mg. (1 mmole) 1,3-diiodopropane in 0.5 ml. of acetonitrile. The mixture is stirred at room temperature for 2.0 hours and the insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration. The filtrate is evaporated and the solid residue obtained is extracted with methylene chloride. The methylene chloride extract is evaporated to give the oily product which is recrystallized from isopropanol-ether.

Workup

  1. customthe insoluble N,N,N-trimethyl-[3-(methylamino)]-1-propanaminium bromide hydrobromide is removed by filtration
  2. customThe filtrate is evaporated
  3. customthe solid residue obtained
  4. extractionis extracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. customis evaporated
  7. customto give the oily product which
  8. customis recrystallized from isopropanol-ether

Sources & evidence

ORD record
ord-67f8a14eaaf646e3aa9f1c0d5f04e3a1
Source dataset
uspto-grants-1978_07
Patent number
US04098726

Reaction notes

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