Ammonia → HCID 67173190, compound

HRID 551155Notes

Reaction equation

HRID 551155 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][C:9]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)([C:12]#[N:13])[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2].N.O>CO.[Ni]>[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][C:9]([CH2:12][NH2:13])([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 67174054HCID 67174054, compound

Product 1

HCID 67173190HCID 67173190, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a heavy wall flask was placed 1-(ethylsulfonyl)-4-(tetrahydro-2H-pyran-4-ylmethyl)piperidine-4-carbonitrile (10) (1.25 g, 4.17 mmol) and 2N ammonia in methanol (50 ml). To this was added Raney nickel slurry in water (1.073 g, 12.52 mmol) and the reaction agitated under hydrogen atmosphere (45 psi) at room temp for 12 hours. The catalyst was filtered off using celite and washed with MeOH (200 ml) and the organics were concentrated in vacuo to give 1-[1-(ethylsulfonyl)-4-(tetrahydro-2H-pyran-4-ylmethyl)piperidin-4-yl]methanamine (11) as a clear semi-solid. MS 304 (M+1)

Workup

  1. customIn a heavy wall flask was placed
  2. filtrationThe catalyst was filtered off
  3. washwashed with MeOH (200 ml)
  4. concentrationthe organics were concentrated in vacuo

Sources & evidence

ORD record
ord-d989d6410b6d4598b19306b80a4020c9
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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