Triethylamine → 1-(4-Benzyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanone

HRID 370657

Reaction equation

HRID 370657 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41](=[O:44])[CH2:42]Br)=[CH:37][CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(OCC)(=O)C>[CH2:27]([O:34][C:35]1[CH:36]=[CH:37][C:38]([C:41](=[O:44])[CH2:42][N:11]2[CH2:10][CH2:9][N:8]([CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:13][CH2:12]2)=[CH:39][CH:40]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70048BenzhydrylpiperazineHCID 105425931-[4-(Benzyloxy)phenyl]-2-bromoethan-1-one

Product 1

HCID 103227601-(4-Benzyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanoneYield 87.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 90 ml of an ethyl acetate solution containing 7.56 g (30 mmol) of 1-diphenylmethylpiperazine and 3.33 g (33 mmol) of triethylamine was added 9.15 g (30 mmol) of p-benzyloxy-α-bromoacetophenone. The resultant mixture was stirred at room temperature for 45 minutes. After addition of 100 ml of ice water, the thus obtained mixture was stirred for about 10 minutes. Precipitated crystals were collected by filtration and then washed successively with water, ethanol and ethyl acetate and thereafter dried to give 12.5 g of 1-(4-benzyloxyphenyl)-2-(4-diphenylmethylpiperazinyl)ethanone (yield: 87.4%).

Workup

  1. customPrecipitated crystals
  2. filtrationwere collected by filtration
  3. washwashed successively with water, ethanol and ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-646b829131ad47e7ae5bb7ff444ff8bf
Source dataset
uspto-grants-1985_07
Patent number
US04528194

Linked notes

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