Potassium Carbonate → 1-[3-[4-[1-(2-Methoxyphenyl)-1-hydroxypropyl]-phenoxy]-propyl]-piperidine

HRID 1583321Notes

Reaction equation

HRID 1583321 reaction equation
[CH2:1]([C:3]([OH:19])([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[O:17][CH3:18])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[CH3:2].Cl[CH2:21][CH2:22][CH2:23][N:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C(=O)([O-])[O-].[K+].[K+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:3]([C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:21][CH2:22][CH2:23][N:24]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]2)=[CH:8][CH:9]=1)([OH:19])[CH2:1][CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 79625Piperidine, 1-(3-chloropropyl)-HCID 14727321alpha-Ethyl-alpha-(2-methoxyphenyl)-4-hydroxy-benzylalcohol

Product 1

HCID 138824471-[3-[4-[1-(2-Methoxyphenyl)-1-hydroxypropyl]-phenoxy]-propyl]-piperidine

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 8857Ethyl AcetateSolvent

Procedure

7.7 g. of α-ethyl-α-(2-methoxyphenyl)-4-hydroxy-benzylalcohol and 6.6 g. of N-(3-chloropropyl)-piperidine in 70 ml. of ethyl acetate, in the presence of 14 g. of anhydrous potassium carbonate and 0.5 g. of tetrabutyl ammonium hydrogensulfate are boiled under reflux for 8 hours. Thereafter the solvent is distilled off under reduced pressure, to the residue water is added, and it is extracted with ether. The ethereal phases are combined, washed with water, a 5% aqueous sodium hydroxide solution and again with water till neutral. The organic phase is dried over anhydrous potassium carbonate, and the solvent is distilled off under reduced pressure. Crystallization of the residue from ethyl acetate yields 9.5 g. of the named compound, melting at 110° to 111° C.

Workup

  1. temperatureunder reflux for 8 hours
  2. distillationThereafter the solvent is distilled off under reduced pressure, to the residue water
  3. additionis added
  4. extractionit is extracted with ether
  5. washwashed with water
  6. dry with materialThe organic phase is dried over anhydrous potassium carbonate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customCrystallization of the residue from ethyl acetate
  9. customyields 9.5 g

Sources & evidence

ORD record
ord-65db5362437f4afab1cb031a2e1ec52a
Source dataset
uspto-grants-1985_11
Patent number
US04551465

Reaction notes

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