Water → 4-(4-Nitrophenyl)piperidine-4-carbonitrile

HRID 1262425Notes

Reaction equation

HRID 1262425 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:22]#[N:23])[CH2:15][CH2:14][N:13](C(=O)C(F)(F)F)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(=O)([O-])[O-].[Na+].[Na+].O>CO>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:22]#[N:23])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962Water2×HCID 10340Sodium CarbonateHCID 54228616HCID 54228616, compound

Product 1

HCID 574160994-(4-Nitrophenyl)piperidine-4-carbonitrileYield 88.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(4-Nitro-phenyl)-1-(2,2,2-trifluoro-acetyl)-piperidine-4-carbonitrile (1.28 g, 3.91 mmol) was suspended in Methanol (50.0 mL) and treated with 2.00 M of Sodium carbonate in Water (20.0 mL, 40.0 mmol) at rt overnight. Water was added to the heterogenous mixture to achieve a solution, then the mixture was partitioned between DCM and brine (50 mL each). Ext. of the aq. with DCM (3×50 mL), followed by washing the org. with brine (50 mL), drying and conc. in vacuo afforded 4-(4-Nitro-phenyl)-piperidine-4-carbonitrile (0.800 g; Yield=88.4) as a white solid. 1H-NMR (DMSO-d6): 8.30 (d, 2H, J=8.8 Hz), 7.83 (d, 2H, J=8.8 Hz), 3.07 (m, 2H), 2.82 (m, 2H), 2.36 (br s, 1H), 2.05 (m, 2H), 1.92 (m, 2H).

Workup

  1. customthe mixture was partitioned between DCM and brine (50 mL each)
  2. washby washing the org
  3. dry with materialwith brine (50 mL), drying and conc. in vacuo

Sources & evidence

ORD record
ord-b0f277ec2a7e421a95440e95dbd6d987
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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