Allyl bromide → HCID 23452551, compound

HRID 1278063Notes

Reaction equation

HRID 1278063 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][CH:7]2[CH2:11][CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:20](Br)[CH:21]=[CH2:22]>CC(CC)=O>[CH2:22]([N:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[CH2:6][C:5]1[CH:12]=[CH:13][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 5138807HCID 5138807, compound

Product 1

HCID 23452551HCID 23452551, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Boil 5 g of 2-(4-chlorobenzyl)pyrrolidine, 3.53 g of anhydrous potassium carbonate, 3.4 g of allyl bromide and 50 ml of ethyl methyl ketone under reflux for 1 hour. Evaporate off the solvent. Take up the residue with 50 ml of water and extract 3 times with, in each case, 30 ml of diethyl ether. Combine the ether phases and dry them over sodium sulfate. Distil off the solvent from the combined ether extract and distil the resulting residue under a vacuum to obtain 5.12 g (85% of theory) of the title compound (b.p. 84° to 87° at 0.005 mm of Hg). m.p. of the picrate (from ethanol): 115° to 117°.

Workup

  1. customEvaporate off the solvent
  2. extractionextract 3 times with, in each case, 30 ml of diethyl ether
  3. dry with materialdry them over sodium sulfate
  4. customDistil off the solvent from the combined ether
  5. extractionextract
  6. customdistil the resulting residue under a vacuum

Sources & evidence

ORD record
ord-7c9301b03d8a4d2885f868c556f9ba05
Source dataset
uspto-grants-1981_07
Patent number
US04279918

Reaction notes

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