Potassium Carbonate → 1-[3-[4-[1-(3-Chlorophenyl)-1-hydroxypropyl]-phenoxy]-propyl]-piperidine

HRID 1583319Notes

Reaction equation

HRID 1583319 reaction equation
[CH2:1]([C:3]([OH:18])([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=1)[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.Cl[CH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C(C(C)=O)C(C)C>[Cl:17][C:13]1[CH:12]=[C:11]([C:3]([C:4]2[CH:5]=[CH:6][C:7]([O:10][CH2:27][CH2:28][CH2:29][N:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:8][CH:9]=2)([OH:18])[CH2:1][CH3:2])[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 138824393-Chloro-4'-hydroxy-alpha-ethyl-benzhydrol

Product 1

HCID 138824401-[3-[4-[1-(3-Chlorophenyl)-1-hydroxypropyl]-phenoxy]-propyl]-piperidine

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

7.9 g. of α-ethyl-α-(3-chlorphenyl)-4-hydroxybenzyl alcohol, 14 g. of anhydrous potassium carbonate and 6.6 g. of N-(3-chloropropyl)-piperidine hydrochloride in 80 ml. of methyl isobutyl ketone are boiled under moderate reflux for three hours. The solvent is distilled off under reduced pressure, to the residue water is added and it is extracted with benzene. The benzene phase is washed with an aqueous potassium hydroxide solution and subsequently with water, dried over anhydrous magnesium sulfate, and evaporated to dryness in vacuo. Crystallization of the residue from n-hexane yields 8.6 g. of the title compound, melting at 80° to 81° C.

Workup

  1. temperatureunder moderate reflux for three hours
  2. distillationThe solvent is distilled off under reduced pressure, to the residue water
  3. additionis added
  4. extractionit is extracted with benzene
  5. washThe benzene phase is washed with an aqueous potassium hydroxide solution and subsequently with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated to dryness in vacuo
  8. customCrystallization of the residue from n-hexane
  9. customyields 8.6 g

Sources & evidence

ORD record
ord-251a74763deb40e2a7da3ac1d652d622
Source dataset
uspto-grants-1985_11
Patent number
US04551465

Reaction notes

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