Ammonia → HCID 57931184, compound

HRID 551160Notes

Reaction equation

HRID 551160 reaction equation
[CH2:1]([S:3]([N:6]1[CH2:11][CH2:10][C:9]([CH2:14][CH:15]2[CH2:19][CH2:18][CH2:17][O: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[CH2:19][CH2:18][CH2:17][O:16]2)[CH2:8][CH2:7]1)(=[O:5])=[O:4])[CH3:2]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 579311911-(Ethylsulfonyl)-4-[(tetrahydro-2-furanyl)methyl]-4-piperidinecarbonitrile

Product 1

HCID 57931184HCID 57931184, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

In a heavy wall flask was placed 1-(ethylsulfonyl)-4-(tetrahydrofuran-2-ylmethyl)piperidine-4-carbonitrile (15, 2 g, 6.98 mmol) and 2N ammonia in methanol (50 ml). To this was added commercially available Raney nickel slurry in water (1.8 g, 20.94 mmol) and the solution 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 combined organics concentrated in vacuo to give 1-[1-(ethylsulfonyl)-4-(tetrahydrofuran-2-ylmethyl)piperidin-4-yl]methanamine (16) as a clear semi-solid. MS 291 (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 combined organics concentrated in vacuo

Sources & evidence

ORD record
ord-d16466a8126c408896b4f3761a16d860
Source dataset
uspto-grants-2011_05
Patent number
US07947714B2

Reaction notes

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