Phosphorus sulfide (P2S5) → 4-(6-Chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino}-2-thioxopiperazine

HRID 2086292Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=O)[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:36]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([N:15]1[CH2:20][CH2:19][N:18]([NH:21][CH:22]3[CH2:27][CH2:26][N:25]([C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[C:17](=[S:36])[CH2:16]1)(=[O:14])=[O:13])[CH:6]=[CH:5]2

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-(6-chloronaphthalene-2-sulfonyl)-1-[1-(4-pyridyl)-4-piperidinylamino}-2-piperazinone (200 mg) in pyridine (10 ml) was combined with phosphorus pentasulfide (80 mg) and stirred at 100° C. for 5 hours. The supernatant of the reaction mixture was concentrated and the residue was purified by a column chromatography on a silica gel (dichloromethane: 10% aqueous ammonia-containing methanol=20:1) to obtain the title compound (35 mg) as a colorless solid.

Workup

concentrationThe supernatant of the reaction mixture was concentrated
customthe residue was purified by a column chromatography on a silica gel (dichloromethane: 10% aqueous ammonia-containing methanol=20:1)

Sources & evidence

ORD record: ord-d570f4a6c5174d6fbad4457da3de72dc
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06723722B1

Reaction notes

Loading…