Lawesson's reagent → N2-methyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarbothioamide

HRID 397668Notes

Reaction equation

HRID 397668 reaction equation
[CH3:1][NH:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>>[CH3:1][NH:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[S:11]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)(=[O:13])=[O:12])=[S:30]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 32008853N2-methyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxamide

Product 1

HCID 57230524N2-methyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarbothioamide

Procedure

The title compound was prepared by a similar method to Example 20 from N2-methyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxamide [see Preparation 43] and Lawesson's reagent. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 0:100 changing to 25:75 (in 5% increments), by volume, ethyl acetate:hexane, to afford N2-methyl-(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarbothioamide as a white solid.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 0:100 changing to 25:75 (in 5% increments), by volume, ethyl acetate

Sources & evidence

ORD record
ord-380bc901aaf54be3a9e785dd8cc82ebc
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

Loading…