1-Phenylpiperazine → HCID 54383782, compound

HRID 274608Notes

Reaction equation

HRID 274608 reaction equation
C(O[C@@:5]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[F:25])([C@H:12]([S:14](Cl)(=[O:16])=[O:15])[CH3:13])[CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1)(=O)C.[C:26]1([N:32]2[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>ClCCl>[F:25][C:19]1[CH:20]=[C:21]([F:24])[CH:22]=[CH:23][C:18]=1[C:5]([CH2:6][N:7]1[CH:11]=[N:10][CH:9]=[N:8]1)=[C:12]([S:14]([N:35]1[CH2:36][CH2:37][N:32]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:33][CH2:34]1)(=[O:15])=[O:16])[CH3:13]

Participants

4

Reactant 2

HCID 70961-PhenylpiperazineHCID 10430695HCID 10430695, compound

Product 1

HCID 54383782HCID 54383782, compoundYield 8.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (15 ml) was dissolved (2R 3R)-3-chlorosulfonyl-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2-butyl acetate (0.5 g). To the solution was added, under ice-cooling, 1-phenylpiperazine (0 27 g) The reaction mixture was stirred for 10 minutes under ice-cooling, which was then concentrated. The concentrate was subjected to a silica gel chromatography (eluent: hexane/ethyl acetate=1/2→ethyl acetate) for purification to give, as the first eluate, 1-[3-(2,4-difluorophenyl)-4-(1H-1,2,4-triazol-1-yl)-2-buten-2-ylsulfonyl]-4-phenylpiperazine (isomer B, Compound 31, 0.05 g) as a pale brown solid substance and, as the second eluate, 1-[3-(2,4-difluorophenyl)-4-(1H-1,2,4-triazol-1-yl)-2-buten-2-ylsulfonyl]-4-phenylpiperazine (isomer A, Compound 30, 0.18 g) as a pale brown solid substance.

Workup

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. temperaturecooling
  4. concentrationwhich was then concentrated
  5. customThe concentrate was subjected to a silica gel chromatography (eluent: hexane/ethyl acetate=1/2→ethyl acetate) for purification

Sources & evidence

ORD record
ord-8d7b8c23f3a74fe28cdb21e624999d36
Source dataset
uspto-grants-1995_02
Patent number
US05389663

Reaction notes

Loading…