Methanol → HCID 20296594, compound

HRID 1389476Notes

Reaction equation

HRID 1389476 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[CH2:4][NH:3][C:2]1=[O:11].O1CC1C[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=1[O:23][C:24]1[CH:29]=[CH:28]C(OC)=CC=1CC1OC1.C[OH:38]>C1(C)C=CC=CC=1>[CH3:22][O:21][C:19]1[CH:20]=[CH:15][C:16]([O:23][CH2:24][CH:29]([OH:38])[CH2:28][N:8]2[CH2:7][CH2:6][C:5]3([O:1][C:2](=[O:11])[NH:3][CH2:4]3)[CH2:10][CH2:9]2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 129541141-Oxa-3,8-diazaspiro(4.5)decan 2-oneHCID 199644222,3-Epoxypropyl4-methoxyphenyl ether

Product 1

HCID 20296594HCID 20296594, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3.4 g 1-oxa-3,8-diazaspiro[4.5]decan-2-one, 2.26 g 2,3-epoxypropyl-p-methoxyphenyl ether, 5 ml methanol and 15 ml toluene is heated at reflux for 24 hours. Evaporation of solvent and recrystallization from ethyl acetate gives 2.7 g 8-[3-(4-methoxyphenoxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one, mp 151°-153°. To a solution of 1 g of 8-[3-(4-methoxyphenoxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one in 5 ml methanol is added 10 ml of 3% hydrochloric acid in methanol. Addition of 200 ml diethyl ether, followed by filtration gives 8-[3-(4-methoxyphenoxy)-2-hydroxypropyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrochloride, mp 198°-203°.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 24 hours
  3. customEvaporation of solvent and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-11ade518f2cf453fba585644aa3f53b5
Source dataset
uspto-grants-1981_01
Patent number
US04244961

Reaction notes

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