Potassium Hydroxide → HCID 86746450, compound

HRID 1645880Notes

Reaction equation

HRID 1645880 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16](=O)[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:30][OH:31].[OH-].[K+]>C(O)C.CO>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16](=[N:30][OH:31])[C:17]2[CH:22]=[CH:21][C:20]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 10090964HCID 10090964, compound

Product 1

HCID 86746450HCID 86746450, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a mixed solution (20 ml) containing 0.8 g of the 1-benzyl-4-[2-(4-pyrrolidinobenzoyl)ethyl]piperidine prepared in Example 59 and 0.7 g of hydroxylamine hydrochloride in ethanol was added a solution (7 ml) of 1.4 g of potassium hydroxide in methanol dropwise with warming at 50°-55° C. The mixture was further heated at 50°-55° C. for one hour, at the end of which time it was added to 200 ml of ice-water. The resulting precipitate was collected by filtration, rinsed and dissolved in dichloromethane. The solution was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to give crude crystals. Recrystallization from dichloromethane-ether yielded 0.55 g of colorless crystals melting at 153°-158° C.

Workup

  1. temperaturewith warming at 50°-55° C
  2. temperatureThe mixture was further heated at 50°-55° C. for one hour, at the end of which time it
  3. filtrationThe resulting precipitate was collected by filtration
  4. washrinsed
  5. dissolutiondissolved in dichloromethane
  6. dry with materialThe solution was dried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customto give crude crystals
  9. customRecrystallization from dichloromethane-ether

Sources & evidence

ORD record
ord-79e21854633c4638a69beef536fdce4d
Source dataset
uspto-grants-1993_01
Patent number
US05177087

Reaction notes

Loading…