Piperidine → Nerbacadol

HRID 980206Notes

Reaction equation

HRID 980206 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+].[CH3:9][C:10]1[O:14][N:13]=[CH:12][C:11]=1[C:15](Cl)=[O:16]>O>[CH3:9][C:10]1[O:14][N:13]=[CH:12][C:11]=1[C:15]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:16]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 14798Sodium Hydroxide2×HCID 27599175-Methyl-1,2-oxazole-4-carbonyl chloride

Product 1

HCID 65865Nerbacadol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.4 mol (34.1 g) of piperidine and 40 ml of 10N sodium hydroxide solution are added dropwise to 0.4 mol (58.2 g) of 5-methyl-4-isoxazolecarboxylic acid chloride, emulsified in 300 ml of water, such that the temperature of the reaction mixture does not rise above 35° C. 40 ml of 2N sodium hydroxide solution are then added and the mixture is extracted with 300 ml methylene chloride. The aqueous phase is extracted once more by shaking with 200 ml of methylene chloride. The combined methylene chloride phases are washed with water and, after drying over sodium sulfate, evaporated to dryness under reduced pressure. N-(5-Methyl-4-isoxazolylcarbonyl)-piperidine is thus obtained, the product having, after recrystallization from methylcyclohexane, a melting point of 40° to 43° C.

Workup

  1. customdoes not rise above 35° C
  2. extractionthe mixture is extracted with 300 ml methylene chloride
  3. extractionThe aqueous phase is extracted once more
  4. washThe combined methylene chloride phases are washed with water
  5. dry with materialafter drying over sodium sulfate
  6. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-15a36ce745f14f2f83fd6588e6fa5ca5
Source dataset
uspto-grants-1987_01
Patent number
US04636513

Reaction notes

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