Ammonium Hydroxide → 4-Piperidinecarboxamide

HRID 1638218Notes

Reaction equation

HRID 1638218 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]#[N:8])[CH2:3][CH2:2]1.[OH-:9].[NH4+]>S(=O)(=O)(O)O>[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:8])=[O:9])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 1382234-Cyanopiperidine

Product 1

HCID 37724-Piperidinecarboxamide

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4-(2-methyl-phenyl-amino)-1-phenylmethyl)-4-piperidine-carbonitrile (17.89 g) was dissolved in 88 ml conc. sulfuric acid and stirred for 3 d at room temperature. The reaction mixture was poured on ice and adjusted to pH 10 by addition of 30% aqueous ammonium hydroxide and extracted three times with dichloromethane. The combined organic layers were dried over sodium sulfate and evaporated to yield 4-(2-methyl-phenyl-amino)-1-phenylmethyl)-4-piperidine-carboxamide (10.35 g) as a brown oil. MS: m/z=324 (M+H)+

Workup

  1. additionThe reaction mixture was poured on ice
  2. extractionextracted three times with dichloromethane
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-b85223e865044235b96316e510b7d2a2
Source dataset
uspto-grants-2000_03
Patent number
US06043366

Reaction notes

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