1-(1,1-Dimethylethyl)-4-piperidinecarbonitrile → HCID 57929945, compound

HRID 1930064Notes

Reaction equation

HRID 1930064 reaction equation
[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([C:11]#[N:12])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH4+]=[S:14]>CO>[C:1]([N:5]1[CH2:10][CH2:9][CH:8]([C:11](=[S:14])[NH2:12])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 579299241-(1,1-Dimethylethyl)-4-piperidinecarbonitrile

Product 1

HCID 57929945HCID 57929945, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 1-tert-butylpiperidine-4-carbonitrile (0.900 g, 5.41 mmol, (prepared as described in WO2008/1017461, Compound XXIV), ammonium sulfide (20 wt % in water, 3.69 mL, 10.8 mmol) and MeOH (9.0 mL) were heated in a CEM® microwave at about 120° C. for about 2 h (250 psi maximum pressure, 10 min ramp, 300 max watts). The mixture was concentrated under a stream of air and the resulting material was purified by flash chromatography on silica gel using DCM/MeOH with 3% NH4OH (8:2) as an eluent to give the title compound (0.140 g, 13%): LC/MS (Table 1, Method a) Rt=0.44 min; MS m/z: 201.1 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated under a stream of air
  2. customthe resulting material was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-379e36c2576443caabbd7c360ffed8c4
Source dataset
uspto-grants-2012_05
Patent number
US08188083B2

Reaction notes

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