Hydrochloric Acid → 1-(alpha-Naphthoxy)-3-(tert.-butylamino)-2-propanol hydroxide

HRID 328883Notes

Reaction equation

HRID 328883 reaction equation
Cl.[C:2]1([O:12][CH2:13][CH:14]([OH:21])[CH2:15][NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1>CCOCC>[OH-:12].[C:2]1([O:12][CH2:13][CH:14]([OH:21])[CH2:15][NH:16][C:17]([CH3:19])([CH3:18])[CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 100618521-(1-Naphthyloxy)-3-(tert-butylamino)-2-propanol

Product 1

HCID 1317107191-(alpha-Naphthoxy)-3-(tert.-butylamino)-2-propanol hydroxide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 6.5 parts of 1-(tert.-butyl)-3-azetidinol and 7.9 parts of α-naphthol 0.2 part of potassium hydroxide was added, and the mixture was heated at 160° C. for 24 hours. The reaction mixture was cooled and then dissolved in 100 parts of ether. The solution was washed twice with 50 parts of 2N-sodium hydroxide aqueous solution and extracted three times with 50 parts of 2N-hydrochloric acid aqueous solution. The extract was washed with 50 parts of ether and made alkaline by addition of 2N-sodium hydroxide aqueous solution. Extraction was conducted three times with 50 parts of benzene, and the extract was dried over anhydrous sodium sulfate. Then benzene was distilled off and the residue was solidified by drying under reduced pressure. The solid residue was subjected to distillation under reduced pressure. As a result 5 parts of 1-(α-naphthoxy)-3-(tert.-butylamino)-2-propanol boiling at 175°-180° C. under 1.5 mm Hg were obtained. A part of the product was dissolved in 5 parts of anhydrous ether and the product was converted to a hydrochloride by adding a hydrochloric acid gas to the resulting ether solution. The hydrochloric was recrystallized twice from a mixed solvent of ethyl acetate and ether. As a result 1-(α-naphthoxy)-3-(tert.-butylamino)-2-propanol hydrochloride having a melting point of 182°-184° C was obtained.

Workup

  1. customwere obtained
  2. customThe hydrochloric was recrystallized twice from a mixed solvent of ethyl acetate and ether

Sources & evidence

ORD record
ord-253251e30d8d436a8b8da50a031070a5
Source dataset
uspto-grants-1977_04
Patent number
US04018824

Reaction notes

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