Dimethylformamide → (2S)-1-[(cyclohexylmethyl)sulfonyl]-2-piperidinecarbonitrile

HRID 397660Notes

Reaction equation

HRID 397660 reaction equation
[CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]([NH2:19])=O)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C(Cl)=O.CN(C)C=O>N1C=CC=CC=1>[CH:1]1([CH2:7][S:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C@H:12]2[C:17]#[N:19])(=[O:9])=[O:10])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 57034239HCID 57034239, compound

Product 1

HCID 57034946(2S)-1-[(cyclohexylmethyl)sulfonyl]-2-piperidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound was prepared by a similar method to Preparation 3 from (2S)-1-[(cyclohexylmethyl)sulfonyl]-2-piperidinecarboxamide [see Preparation 26], oxalyl chloride, dimethylformamide and pyridine. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 80:20 changing to 20:80, by volume (in 10% increments), hexane:ethyl acetate to afford (2S)-1-[(cyclohexylmethyl)sulfonyl]-2-piperidinecarbonitrile as an oil.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 80:20 changing to 20:80, by volume (in 10% increments), hexane

Sources & evidence

ORD record
ord-c75e56e16bf0475492948f8f99c876c0
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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