Ammonium Hydroxide → 1-Benzyl-4-((4-chlorophenyl)amino)piperidine-4-carboxamide

HRID 556959Notes

Reaction equation

HRID 556959 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([NH:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)([C:14]#[N:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:24].[NH4+]>S(=O)(=O)(O)O>[CH2:1]([N:8]1[CH2:9][CH2:10][C:11]([NH:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)([C:14]([NH2:15])=[O:24])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 704181-Benzyl-4-((4-chlorophenyl)amino)piperidine-4-carbonitrile

Product 1

HCID 705871-Benzyl-4-((4-chlorophenyl)amino)piperidine-4-carboxamideYield 71%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To 1-Benzyl-4-(4-chloro-phenylamino)-piperidine-4-carbonitrile (1.97 g, 6.05 mmol) was added concentrated sulfuric acid (50 ml). The reaction stirred at room temperature as an orange homogeneous solution. After 24 hours the reaction was cooled to 0° C. and very slowly poured into concentrated ammonium hydroxide in ice. The precipitate was filtered and washed with water to give a white solid (202 mg, 71%).

Workup

  1. temperatureAfter 24 hours the reaction was cooled to 0° C.
  2. filtrationThe precipitate was filtered
  3. washwashed with water

Sources & evidence

ORD record
ord-ed264d869b3a42b394d7c085ae30a8f3
Source dataset
uspto-grants-2011_11
Patent number
US08058287B2

Reaction notes

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