Allyl bromide → Alimadol

HRID 1657536Notes

Reaction equation

HRID 1657536 reaction equation
[C:1]1([C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([O:17][CH3:18])[CH2:8][CH2:9][NH:10][C:11](=O)[C:12](F)(F)F)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:25](Br)C=C.[OH-].[K+]>CC(C)=O>[C:1]1([C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([O:17][CH3:18])[CH2:8][CH2:9][NH:10][CH2:11][CH:12]=[CH2:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 14797Potassium HydroxideHCID 21534186HCID 21534186, compound

Product 1

HCID 176882AlimadolYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

16.7 g. of N-(3,3-diphenyl-3-methoxypropyl)-trifluoroacetamide, prepared according to Example 4, and 24.2 g. of allyl bromide in 150 ml. of anhydrous acetone are heated to 50°C. and 11.2 g. of powdered potassium hydroxide are added. The mixture is then boiled for 5 minutes and the solvent is distilled off in vacuo. The residue is boiled for one hour with 100 ml. of water and 100 ml. of methanol and is worked up as in Example 4. 13.1 g. of 1,1-diphenyl-1-methoxy-3-allylaminopropane of melting point 45° to 50°C. are obtained, corresponding to a yield of 93% of theory.

Workup

  1. distillationthe solvent is distilled off in vacuo
  2. waitThe residue is boiled for one hour with 100 ml

Sources & evidence

ORD record
ord-60efb1f5ec024113a75fdb0fceebe1bb
Source dataset
uspto-grants-1976_06
Patent number
US03960960

Reaction notes

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