Allyl bromide → HCID 20240740, compound

HRID 1583700Notes

Reaction equation

HRID 1583700 reaction equation
[CH3:1][CH:2]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])[CH2:3][N:4]1[CH2:8][CH2:7][CH2:6][CH2:5]1.[CH2:17]([Br:20])[CH:18]=[CH2:19]>C(OCC)(=O)C>[Br-:20].[CH2:19]([N+:4]1([CH2:3][CH:2]([CH3:1])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH2:8][CH2:7][CH2:6][CH2:5]1)[CH:18]=[CH2:17]

Participants

4

Reactant 2

HCID 7841Allyl bromideHCID 20240737HCID 20240737, compound

Product 1

HCID 20240740HCID 20240740, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 51 g of N-[2-methyl-3-(o-methyl-phenyl)-propyl]-pyrrolidine and 58 g of allyl bromide in 200 ml of ethyl acetate is refluxed for 5 hours. The product precipitates as a resin. After the ethyl acetate has been decanted, the crude product is triturated several times with ethyl acetate. Supernatant solvent is decanted. Finally, the product is triturated with n-pentane and the solvent decanted. The oil which remains is freed from solvent residues in a rotary evaporator. There remains 60 g of N-allyl-N-[2-methyl-3-(o-methyl-phenyl)-propyl]-pyrrolidinium bromide as a brown resin.

Workup

  1. customThe product precipitates as a resin
  2. customAfter the ethyl acetate has been decanted
  3. customthe crude product is triturated several times with ethyl acetate
  4. customSupernatant solvent is decanted
  5. customFinally, the product is triturated with n-pentane
  6. customthe solvent decanted
  7. customThe oil which remains is freed from solvent residues in a rotary evaporator

Sources & evidence

ORD record
ord-8c34436e06e2463f839ab12401028216
Source dataset
uspto-grants-1985_11
Patent number
US04554006

Reaction notes

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