Semicarbazide hydrochloride → HCID 72440645, compound

HRID 1269475Notes

Reaction equation

HRID 1269475 reaction equation
[CH2:1]([C:3]1([CH3:23])[CH:8]([CH3:9])[C:7](=O)[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[N:4]1[O:14][CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])[CH3:2].Cl.[NH2:25][NH:26][C:27]([NH2:29])=[O:28]>CO.[OH-].[K+].O>[CH2:1]([C:3]1([CH3:23])[CH:8]([CH3:9])[C:7](=[N:25][NH:26][C:27]([NH2:29])=[O:28])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[N:4]1[O:14][CH:15]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[CH3:16])[CH3:2]

Participants

6

Reactant 2

HCID 11236Semicarbazide hydrochlorideHCID 223418482,6-Diethyl-2,3,6-trimethyl-1-(1-phenylethoxy)piperidin-4-one2×

Product 1

HCID 72440645HCID 72440645, compoundYield 98.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 14797Potassium HydroxideSolvent2×

Procedure

2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-4-oxopiperidine prepared according to DE 199 09 767 A1 is dissolved in methanol containing 10% by weight of KOH and stirred for 5 hours at room temperature. Methanol is evaporated, the residue is washed with water and dried in vacuo. To a solution of 6.4 g (0.02 mol) 2,6-diethyl-2,3,6-trimethyl-1-(1-pheyl-ethoxy)-piperidine-4-one in 20 ml methanol are added 3.3 g (0.03 mol) semicarbazide hydrochloride and 1.67 g (0.025 mol) KOH (85%). The mixture is stirred under reflux 5 h and then diluted with 200 ml water. The precipitate is extracted into 100 ml of dichloromethane, the organic layer is washed with water, dryied over MgSO4 and evaporated to give 7.8 g (98.8%) of the title compound as a slightly yellow resin.

Workup

  1. customMethanol is evaporated
  2. washthe residue is washed with water
  3. customdried in vacuo
  4. stirringThe mixture is stirred
  5. temperatureunder reflux 5 h
  6. extractionThe precipitate is extracted into 100 ml of dichloromethane
  7. washthe organic layer is washed with water
  8. customevaporated

Sources & evidence

ORD record
ord-774c324ca0e14caa8d4eef541da34bac
Source dataset
uspto-grants-2007_04
Patent number
US07199245B2

Reaction notes

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