Ammonium Hydroxide → 4-Piperidinecarboxamide

HRID 1638216Notes

Reaction equation

HRID 1638216 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-(3-methyl-phenyl-amino)-1-phenylmethyl)-4-piperidine-carbonitrile (15.48 g) was dissolved in 77 ml conc. sulfuric acid and stirred for 18 h at room temperature. After cooling to 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, filtered and evaporated to yield off-white crystalls of 4-(3-methyl-phenyl-amino)-1-phenylmethyl)-4-piperidine-carboxamide (14.46), m.p. 106.1-108.6° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. additionthe reaction mixture was poured on ice
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-1a48068b6c204411ae85cfd5c4ca0f4a
Source dataset
uspto-grants-2000_03
Patent number
US06043366

Reaction notes

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