1-Chloro-3-iodopropane → 3-[N'-(3-Chloropropyl)-N'-methylamino]-N,N,N-trimethyl-1-propanaminium Iodide

HRID 866304Notes

Reaction equation

HRID 866304 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][Cl:15]>C(#N)C>[I-: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 813631-Chloro-3-iodopropaneHCID 21444211N,N,N-Trimethyl-3-(methylamino)propan-1-aminium bromide

Product 1

HCID 213163753-[N'-(3-Chloropropyl)-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 205 mg. (1 mmole) of 3-iodo-1-chloropropane 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 to afford 90 mg. (52%) of product; m.p. 93° (dec.); NMR δ: 2.2 (3H, S, --NCH3); 3.46 (9H, S, --+NMe3).

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
  9. customto afford 90 mg

Sources & evidence

ORD record
ord-d0fa251a80b445118b314176b7912e4d
Source dataset
uspto-grants-1978_07
Patent number
US04098726

Reaction notes

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