Ammonium Hydroxide → 4-Piperidinecarboxamide

HRID 1638212Notes

Reaction equation

HRID 1638212 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-(p-tolyl-amino)-1-phenylmethyl)-4-piperidine-carbonitrile (4.58 g) was dissolved in 25 ml conc. sulfuric acid and stirred for 70 h at room temperature. Then 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, filtered and evaporated to yield 4-(p-tolyl-amino)-1-phenylmethyl)-4-piperidine-carboxamide as an off-white powder (5.11 g), m.p. 167.5-169° C.

Workup

  1. additionThen the 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. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-f6568a2829df404691b130278bdd20fe
Source dataset
uspto-grants-2000_03
Patent number
US06043366

Reaction notes

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