Allyl bromide → N-(4-chlorophenyl)-N-[1-(2-propenyl)-4-piperidinyl]benzeneacetamide hydrochloride

HRID 2049066Notes

Reaction equation

HRID 2049066 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:32][CH:33]=[CH2:34]>C1C=CC=CC=1>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]([CH:18]2[CH2:23][CH2:22][N:21]([CH2:34][CH:33]=[CH2:32])[CH2:20][CH2:19]2)[C:9](=[O:17])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 162188N-(4-Chlorophenyl)-N-4-piperidinylbenzeneacetamide

Product 1

HCID 23339063N-(4-chlorophenyl)-N-[1-(2-propenyl)-4-piperidinyl]benzeneacetamide hydrochloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred solution of 5 parts of N-(4-chlorophenyl)-N-(4-piperidinyl)benzeneacetamide, 3.8 parts of N,N-diethylethanamine in 200 parts of benzene are added portionwise 5 parts of 3-bromo-1-propene. After the addition is complete, the whole is heated for 21 hours at a temperature between 50°-60° C. The reaction mixture is cooled and filtered. The filtrate is washed successively with water, sodium hydrogen carbonate solution and water, dried over potassium carbonate and evaporated. The oily residue is converted into the hydrochloride salt in 1,1'-oxybisethane and 2-propanone, yielding 4 parts of N-(4-chlorophenyl)-N-[1-(2-propenyl)-4-piperidinyl]benzeneacetamide hydrochloride; mp. 225.5° C.

Workup

  1. additionAfter the addition
  2. temperaturethe whole is heated for 21 hours at a temperature between 50°-60° C
  3. temperatureThe reaction mixture is cooled
  4. filtrationfiltered
  5. washThe filtrate is washed successively with water, sodium hydrogen carbonate solution and water
  6. dry with materialdried over potassium carbonate
  7. customevaporated

Sources & evidence

ORD record
ord-1a0536b7543544f6b0e0bc518effd064
Source dataset
uspto-grants-1980_04
Patent number
US04196210

Reaction notes

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