Potassium Hydroxide → HCID 14501712, compound

HRID 1904677Notes

Reaction equation

HRID 1904677 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=1)[O:7][CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1.[OH:22][C:23]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.[OH-].[K+]>O.C(O)C>[OH:22][C:23]1([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:28][CH2:27][N:26]([CH2:3][C:4]2[CH:5]=[C:6]([CH:19]=[CH:20][CH:21]=2)[O:7][CH2:8][C:9]2[CH:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 963874-Phenylpiperidin-4-olHCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

Product 1

HCID 14501712HCID 14501712, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 3.2 g (0.01 mol) 2-(3-chloromethyl-phenoxymethyl)quinoline hydrochloride, 1.7 g (0.01 mol) 4-hydroxy-4-phenylpiperidine and 1.2 g (0.02 mol) KOH in 5 ml of H2O and 50 ml ethanol was heated over steam bath for a period of 3 hours. Reaction mixture was concentrated to dryness and slurried into water, and extracted with methylene chloride. The methylene chloride extract dried over MgSO4 and concentrated to dryness under reduced pressure to obtain solid. Repeated recrystallization from isopropanol and acetronitrite gave desired product 2 g, m.p. 123°-225° C.

Workup

  1. temperaturewas heated over steam bath for a period of 3 hours
  2. customReaction mixture
  3. concentrationwas concentrated to dryness
  4. extractionextracted with methylene chloride
  5. extractionThe methylene chloride extract
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness under reduced pressure
  8. customto obtain solid
  9. customrecrystallization from isopropanol

Sources & evidence

ORD record
ord-026a3df1162f41c986cf70422c51ef47
Source dataset
uspto-grants-1989_06
Patent number
US04839369

Reaction notes

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