Acetone → HCID 13277417, compound

HRID 1075854Notes

Reaction equation

HRID 1075854 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[OH:13].[Cl:14][CH2:15][CH:16]([OH:26])[CH2:17][N:18]1[CH:23]([CH3:24])[CH2:22][CH2:21][CH2:20][CH:19]1[CH3:25].C(=O)([O-])[O-].[K+].[K+].CC(C)=O>CN(C)C=O>[ClH:14].[CH3:25][CH:19]1[CH2:20][CH2:21][CH2:22][CH:23]([CH3:24])[N:18]1[CH2:17][CH:16]([OH:26])[CH2:15][O:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 11430Potassium CarbonateHCID 156497362-[(Thiophen-2-yl)methyl]phenolHCID 20373484HCID 20373484, compound

Product 1

HCID 13277417HCID 13277417, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.9 g of 2-(2-thienylmethyl)phenol, 2.3 g of 1-chloro-3-(2,6-dimethylpiperidino)-2-propanol, 1.4 g of anhydrous potassium carbonate, 30 ml of acetone and 20 ml of dimethylformamide is refluxed with stirring for 20 hours. The insoluble matter is then filtered off, and the filtrate is concentrated. To the residue is added ether, and the ethereal solution is extracted with two 50 ml portions of 10% hydrochloric acid. The aqueous layer is made alkaline with sodium hydroxide, and the separated oil is extracted twice with ether. The ether layer is dried over anhydrous potassium carbonate, and the solvent is removed. The residue is purified by column chromatography and converted into the hydrochloride in the same manner as in above method (a) to give 1.5 g of 1-(2,6-dimethylpiperidino)-3-[2-(2-thienylmethyl)phenoxy]-2-propanol hydrochloride, melting at 152°-153°C.

Workup

  1. temperatureis refluxed
  2. filtrationThe insoluble matter is then filtered off
  3. concentrationthe filtrate is concentrated
  4. additionTo the residue is added ether
  5. extractionthe ethereal solution is extracted with two 50 ml portions of 10% hydrochloric acid
  6. extractionthe separated oil is extracted twice with ether
  7. dry with materialThe ether layer is dried over anhydrous potassium carbonate
  8. customthe solvent is removed
  9. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-d1204881bcc9479e8ce700e3073b25fd
Source dataset
uspto-grants-1976_05
Patent number
US03954776

Reaction notes

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