Ammonia → HCID 57931192, compound

HRID 551151Notes

Reaction equation

HRID 551151 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][C:9]([CH2:14][CH:15]([CH3:17])[CH3:16])([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[CH2:7][CH2:8][C:9]([CH2:12][NH2:13])([CH2:14][CH:15]([CH3:16])[CH3:17])[CH2:10][CH2:11]1)(=[O:4])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 57931193HCID 57931193, compound

Product 1

HCID 57931192HCID 57931192, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a heavy wall flask was placed 1-(ethylsulfonyl)-4-isobutylpiperidine-4-carbonitrile (4, 1.4 g, 5.42 mmol) 2N ammonia in methanol (50 ml). To this was added commercially available Raney nickel slurry in water (1.393 g, 16.26 mmol). This was then 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). The organics were concentrated in vacuo to give 1-[1-(ethylsulfonyl)-4-isobutylpiperidin-4-yl]methanamine (5) as a clear oil. MS 263 (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-08d8db12aac146feaf365b28648010c3
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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