4-(Morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidine-4-carbonitrile → {[4-(Morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidin-4-yl]methyl}amine

HRID 2102390Notes

Reaction equation

HRID 2102390 reaction equation
[N:1]1([C:7]([C:9]2([C:21]#[N:22])[CH2:14][CH2:13][N:12]([S:15]([CH2:18][CH2:19][CH3:20])(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1>N.CO.[Ni]>[N:1]1([C:7]([C:9]2([CH2:21][NH2:22])[CH2:14][CH2:13][N:12]([S:15]([CH2:18][CH2:19][CH3:20])(=[O:17])=[O:16])[CH2:11][CH2:10]2)=[O:8])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 578030894-(Morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidine-4-carbonitrile

Product 1

HCID 57803091{[4-(Morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidin-4-yl]methyl}amineYield 99%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A mixture of 4-(morpholin-4-ylcarbonyl)-1-(propylsulfonyl)piperidine-4-carbonitrile (I-4) (3.29 g, 10 mmole) and Raney Ni (2 g) in 2M NH3-MeOH (100 mL) was hydrogenated (55 psi) overnight at room temperature. Next morning, LCMS indicated that the hydrogenation was completion. Raney Ni was filtered and washed with MeOH (5×60 mL). The collected MeOH solution was concentrated to afford the title amine (I-5) (3.29 g, 99%) as a white solid. Analytical LCMS: single peak (214 nm), 1.723 min.

Workup

  1. custom(55 psi) overnight
  2. customat room temperature
  3. filtrationRaney Ni was filtered
  4. washwashed with MeOH (5×60 mL)
  5. concentrationThe collected MeOH solution was concentrated

Sources & evidence

ORD record
ord-df2ba7957f6d4159aaa5b01dcfbe01b7
Source dataset
uspto-grants-2009_08
Patent number
US07576083B2

Reaction notes

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