Ammonium Chloride → HCID 19887350, compound

HRID 654450Notes

Reaction equation

HRID 654450 reaction equation
[C:1]1([C:7]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[CH:8][CH2:9][N:10]2[CH2:15][CH2:14][C:13]([C:21]#[CH:22])([O:16][C:17](=[O:20])[NH:18][CH3:19])[CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[NH4+]>[O-]CC.[Na+]>[C:23]1([C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:8][CH2:9][N:10]2[CH2:15][CH2:14][C:13]3([O:16][C:17](=[O:20])[N:18]([CH3:19])[C:21]3=[CH2:22])[CH2:12][CH2:11]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 19887347HCID 19887347, compound

Product 1

HCID 19887350HCID 19887350, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 2723922Sodium ethoxideSolvent

Procedure

9.4 g of 1-(3,3-diphenyl-2-propenyl)-4-ethynyl-4-methylcarbamoyloxypiperidine are refluxed in 100 ml of 0.05 mol/liter ethanolic sodium ethoxide solution under argon for 3 hours. After cooling down, the alkoxide is decomposed by adding aqueous ammonium chloride solution and the solvent is distilled off under reduced pressure. After adding benzene and water to the residue, the benzene layer is separated and dried, then evaporated under reduced pressure. After recrystallizing the solid evaporation residue from ethanol, the title compound is obtained in 71.7% yield, m.p.: 126°-127° C.

Workup

  1. temperatureAfter cooling down
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionAfter adding benzene and water to the residue
  4. customthe benzene layer is separated
  5. customdried
  6. customevaporated under reduced pressure
  7. customAfter recrystallizing
  8. customthe solid evaporation residue from ethanol

Sources & evidence

ORD record
ord-846cb24d5269447a8ac82b3b52fcf93f
Source dataset
uspto-grants-1992_07
Patent number
US05132303

Reaction notes

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