Acrylamide → HCID 86751319, compound

HRID 1418579Notes

Reaction equation

HRID 1418579 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:7].[C:33]([NH2:37])(=[O:36])[CH:34]=[CH2:35]>C1(C)C=CC=CC=1>[F:30][C:27]([F:28])([F:29])[C:25]1[CH:24]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:31])[F:32])[CH:26]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:35][CH2:34][C:33](=[O:36])[NH2:37])[CH2:10][C@H:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:7]

Participants

4

Reactant 2

HCID 6579Acrylamide2×HCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine

Product 1

HCID 86751319HCID 86751319, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (150 mg), acrylamide (24 mg) in toluene (1.5 ml) was stirred at room temperature for 1 hour and then was refluxed for 5 hours. After additional acrylamide (24 mg) was added, the whole mixture was refluxed for 3 hours and evaporated under reduced pressure. The obtained residue was purified by column chromatography on a silica gel eluting with a mixture of ethyl acetate and methanol (10:1) to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-4-(2-carbamoylethyl)-2-(1H-indol-3-yl-methyl)piperazine (89 mg).

Workup

  1. temperaturewas refluxed for 5 hours
  2. temperaturethe whole mixture was refluxed for 3 hours
  3. customevaporated under reduced pressure
  4. customThe obtained residue was purified by column chromatography on a silica gel eluting with a mixture of ethyl acetate and methanol (10:1)

Sources & evidence

ORD record
ord-075aa576baec4052b742df1b55beb5db
Source dataset
uspto-grants-1999_03
Patent number
US05883098

Reaction notes

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