HCID 59003518, compound → HCID 59003494, compound

HRID 1169830Notes

Reaction equation

HRID 1169830 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2([C:20]#[N:21])[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH2:18][CH3:19])(=[O:16])=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1>N.CO.[Ni]>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2([CH2:20][NH2:21])[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH2:18][CH3:19])(=[O:16])=[O:15])[CH2:12][CH2:13]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 59003518HCID 59003518, compound

Product 1

HCID 59003494HCID 59003494, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21705897Ammonia methanolSolvent

Procedure

A 4-(6-methylpyridin-2-yl)-1-(propylsulfonyl)piperidine-4-carbonitrile (II-4A) (2.77 g, 9 mmole) and Raney-Ni (1.5 g) in ammonia-MeOH (2M, 80 mL) was hydrogenated under H2 (55 psi) at rt o/n. After this time LCMS indicated that the reaction was completion. The catalyst was filtered and washed with MeOH (6×60 mL). The MeOH solution was concentrated on a rotary evaporator to afford {[4-(6-methylpyridin-2-yl)-1-(propylsulfonyl)piperidin-4-yl]methyl}amine (II-5) as a liquid. Anal LCMS: single peak (214 nm), 1.931 min. This product was used in next step reaction without further purification.

Workup

  1. customwas hydrogenated under H2 (55 psi) at rt
  2. filtrationThe catalyst was filtered
  3. washwashed with MeOH (6×60 mL)
  4. concentrationThe MeOH solution was concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-e8cc6324769f4569883c0ea9ab3b6fb5
Source dataset
uspto-grants-2010_11
Patent number
US07825135B2

Reaction notes

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