m-Chloroperbenzoic acid → N-[(2E)-4-[4-(2,3-Dichlorophenyl)-1-oxido-1-piperazinyl]-2-buten-1-yl]-4-(2-pyridinyl)benzamide

HRID 404575Notes

Reaction equation

HRID 404575 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13]([NH:15][CH2:16]/[CH:17]=[CH:18]/[CH2:19][N:20]3[CH2:25][CH2:24][N:23]([C:26]4[C:31]([Cl:32])=[C:30]([Cl:33])[CH:29]=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)=[O:14])=[CH:11][CH:12]=2)[CH:6]=1.ClC1C=CC=C(C(OO)=[O:42])C=1>ClCCl>[Cl:32][C:31]1[C:30]([Cl:33])=[CH:29][CH:28]=[CH:27][C:26]=1[N:23]1[CH2:24][CH2:25][N+:20]([O-:42])([CH2:19]/[CH:18]=[CH:17]/[CH2:16][NH:15][C:13](=[O:14])[C:10]2[CH:11]=[CH:12][C:7]([C:5]3[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=3)=[CH:8][CH:9]=2)[CH2:21][CH2:22]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11477180N-[(2E)-4-[4-(2,3-Dichlorophenyl)-1-piperazinyl]-2-buten-1-yl]-4-(2-pyridyl)-benzamidedihydrochloride

Product 1

HCID 44427824N-[(2E)-4-[4-(2,3-Dichlorophenyl)-1-oxido-1-piperazinyl]-2-buten-1-yl]-4-(2-pyridinyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of PG01037, see U.S. 2006/0106030 (288 mg, 0.60 mmol) in 10 mL dichloromethane was treated at 0° C. with meta-chloroperbenzoic acid (0.16 g, 77%, 0.72 mmol). After stirring for 16 h at room temperature, the reaction mixture was successively washed with saturated sodium bicarbonate solution, H2O and brine and dried with sodium sulphate. The volatiles were removed in vacuo and the residue was purified by preparative thin layer chromatography. Yield: 93 mg (32%). Mp. (hydrochloride): foam. 1H NMR (CD3OD): δ 3.23-3.29 (m, 4H), 3.50-3.61 (m, 4H), 3.99 (d, J 6.5, 1H), 4.13 (d, J 4.6, 1H), 6.04-6.18 (m, 2H), 7.18 (dd, J 7.8, 3.9, 1H), 7.24-7.28 (m, 2H), 7.40 (m, 1H), 7.91-7.93 (m, 2H), 7.99 (d, J 8.4, 2H), 8.06 (d, J 8.7, 2H), 8.64 (dt, J 4.8, 1.2, 1H). 13C NMR (CDCl3): δ 41.0, 45.5, 63.5, 72.0, 119.3, 120.0, 121.6, 123.1, 125.4, 127.0, 127.3, 127.7, 128.0, 133.8, 134.6, 137.8, 137.9, 142.2, 149.3, 150.1, 156.4, 168.3. Anal. (C26H26Cl2N4O2:2HCl.0.5H2O) C, H, N.

Workup

  1. washthe reaction mixture was successively washed with saturated sodium bicarbonate solution, H2O and brine
  2. dry with materialdried with sodium sulphate
  3. customThe volatiles were removed in vacuo
  4. customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-decf329572df413ba06d6dbcb70c2ceb
Source dataset
uspto-grants-2014_06
Patent number
US08748608B2

Reaction notes

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