4-(Cyclopropylmethyl)-1-(ethylsulfonyl)piperidine-4-carbonitrile → 1-[4-(Cyclopropylmethyl)-1-(ethylsulfonyl)piperidin-4-yl]methanamine

HRID 502893Notes

Reaction equation

HRID 502893 reaction equation
[CH:1]1([CH2:4][C:5]2([C:16]#[N:17])[CH2:10][CH2:9][N:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[CH2:7][CH2:6]2)[CH2:3][CH2:2]1>N.CO.[Ni]>[CH:1]1([CH2:4][C:5]2([CH2:16][NH2:17])[CH2:6][CH2:7][N:8]([S:11]([CH2:14][CH3:15])(=[O:13])=[O:12])[CH2:9][CH2:10]2)[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 594281864-(Cyclopropylmethyl)-1-(ethylsulfonyl)piperidine-4-carbonitrile

Product 1

HCID 686201561-[4-(Cyclopropylmethyl)-1-(ethylsulfonyl)piperidin-4-yl]methanamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A solution of 4-(cyclopropylmethyl)-1-(ethylsulfonyl)piperidine-4-carbonitrile (I-4, 3.1 mg, 11.1 mmol) in 2 M NH3/MeOH (50 mL) was treated with excess Raney Ni and agitated under an atmosphere of H2 (40 psi) in a Parr apparatus. After 5 h, the reaction was filtered through Celite (MeOH wash) and concentrated under reduced pressure to afford 1-[4-(cyclopropylmethyl)-1-(ethylsulfonyl)-piperidin-4-yl]methanamine (I-5, M+H+=261.2) as a yellow oil. This material was used in subsequent reactions without further purification.

Workup

  1. filtrationthe reaction was filtered through Celite (MeOH wash)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-09d675b5db4d4b7c8294c54422a51ea9
Source dataset
uspto-grants-2010_08
Patent number
US07776886B2

Reaction notes

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