Allyl bromide → N-[2-n-Pentyl-3-(2,4-dichlorophenyl)-prop-2-en-1-yl]-N-allyl-pyrrolidinium bromide

HRID 2418269Notes

Reaction equation

HRID 2418269 reaction equation
[CH2:1]([C:6](=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])[CH2:7][N:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:22]([Br:25])[CH:23]=[CH2:24]>C(O)(=O)C>[Br-:25].[CH2:1]([C:6](=[CH:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])[CH2:7][N+:8]1([CH2:24][CH:23]=[CH2:22])[CH2:12][CH2:11][CH2:10][CH2:9]1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 54067199HCID 54067199, compound

Product 1

HCID 86739637N-[2-n-Pentyl-3-(2,4-dichlorophenyl)-prop-2-en-1-yl]-N-allyl-pyrrolidinium bromideYield 53.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

19 g of (IV) and 14.5 g of allyl bromide in 200 ml of glacial acetic acid were refluxed for 5 hours, the mixture was cooled, and the liquid product which separated out was triturated with ethyl acetate. The product which crystallized out was filtered off under suction, washed with ethyl acetate and dried under reduced pressure. 14 g of (V) of melting point 109° C. were obtained (compound No. 3a).

Workup

  1. temperaturethe mixture was cooled
  2. customthe liquid product which separated out
  3. customwas triturated with ethyl acetate
  4. customThe product which crystallized out
  5. filtrationwas filtered off under suction
  6. washwashed with ethyl acetate
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-7965937573014f8fbff04de36f2e1b07
Source dataset
uspto-grants-1984_09
Patent number
US04472412

Reaction notes

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