Nanofin → HCID 13277417, compound

HRID 1075853Notes

Reaction equation

HRID 1075853 reaction equation
[Cl:1][CH2:2][CH:3]([OH:18])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1.[CH3:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([CH3:26])[NH:21]1>C(O)C>[ClH:1].[CH3:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH:22]([CH3:26])[N:21]1[CH2:2][CH:3]([OH:18])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH2:12][C:13]1[S:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 68843NanofinHCID 21541296HCID 21541296, compound

Product 1

HCID 13277417HCID 13277417, compoundYield 53.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2.8 g of 1-chloro-3[2-(2-thienylmethyl)phenoxy]-2-propanol, 2.3 g of 2,6-dimethylpiperidine in 30 ml of ethanol is refluxed for 15 hours. The ethanol is then removed, and the residue is dissolved in ether. The insoluble matter is filtered off, and the filtrated is extracted with two 50 ml portions of 10% hydrochloric acid. The aqueous layer is made alkaline with sodium hydroxide, and separated oil is extracted with ether. The ether layer is dried over anhydrous potassium carbonate, and the solvent is removed. The residue (crude product) is purified by column chromatography and converted into the hydrochloride in the same manner as in above method (a) to give 2.1 g of 1-(2,6-dimethylpiperidino)-3-[2-(2-thienylmethyl)phenoxy]-2-propanol hydrochloride as colorless crystals, melting at 152°-153°C.

Workup

  1. customThe ethanol is then removed
  2. dissolutionthe residue is dissolved in ether
  3. filtrationThe insoluble matter is filtered off
  4. extractionthe filtrated is extracted with two 50 ml portions of 10% hydrochloric acid
  5. customseparated oil
  6. extractionis extracted with ether
  7. dry with materialThe ether layer is dried over anhydrous potassium carbonate
  8. customthe solvent is removed
  9. customThe residue (crude product) is purified by column chromatography

Sources & evidence

ORD record
ord-f2b48cea1309470eb860e7313c36445d
Source dataset
uspto-grants-1976_05
Patent number
US03954776

Reaction notes

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