Pyridine → N-(4-Cyano-benzyl)-N-[4-(4-phenyl-piperazine-1-carbonyl)-phenyl]-benzenesulfonamide

HRID 2380965Notes

Reaction equation

HRID 2380965 reaction equation
[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([C:13]([C:15]3[CH:20]=[CH:19][C:18]([NH:21][CH2:22][C:23]4[CH:30]=[CH:29][C:26]([C:27]#[N:28])=[CH:25][CH:24]=4)=[CH:17][CH:16]=3)=[O:14])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:31]1([S:37](Cl)(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.N1C=CC=CC=1>ClCCl>[C:27]([C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:21]([C:18]2[CH:19]=[CH:20][C:15]([C:13]([N:10]3[CH2:11][CH2:12][N:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:8][CH2:9]3)=[O:14])=[CH:16][CH:17]=2)[S:37]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:39])=[O:38])=[CH:30][CH:29]=1)#[N:28]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 67130691HCID 67130691, compound

Product 1

HCID 46181290N-(4-Cyano-benzyl)-N-[4-(4-phenyl-piperazine-1-carbonyl)-phenyl]-benzenesulfonamideYield 27%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-{[4-(4-Phenyl-piperazine-1-carbonyl)-phenylamino]-methyl}-benzonitrile (50 mg, 0.13 mmol), phenylsulfonylchloride (80 mg, 0.42 mmol) and pyridine (0.04 mL, 0.44 mmol) in dichloromethane (5 ml) was heated to reflux for 16 hours. The reaction mixture was cooled to room temperature and the quenched by the addition of water (4 ml). The organics were collected, dried over magnesium sulfate and concentrated in vacuo The residue was purified by preparative thin layer chromatography (dichloromethane/ethyl acetate 1:1) to afford the title compound as a white solid (16.4 mg, 27% yield). HPLC retention time 6.71 min. Mass spectrum (ES+) m/z 475 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 16 hours
  3. customthe quenched by the addition of water (4 ml)
  4. customThe organics were collected
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo The residue
  7. customwas purified by preparative thin layer chromatography (dichloromethane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-345c990555cf44f4abb90f80a742332e
Source dataset
uspto-grants-2012_09
Patent number
US08258138B2

Reaction notes

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