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

HRID 1706747Notes

Reaction equation

HRID 1706747 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-0690435503c5469aaea913ceabe6f7ee
Source dataset
uspto-grants-1980_06
Patent number
US04208418

Reaction notes

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