Hydrochloric Acid → 8-[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrochloride

HRID 1389478노트

반응식

HRID 1389478 반응식
[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].[OH:12][CH:13]([CH:16]1[O:21][C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17]1)[CH2:14]Br.C(N(CC)CC)C.[ClH:33]>CO.C(OCC)C.O.CN(C)C=O>[ClH:33].[O:21]1[C:20]2[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=2[O:18][CH2:17][CH:16]1[CH:13]([OH:12])[CH2:14][N:8]1[CH2:7][CH2:6][C:5]2([O:1][C:2](=[O:11])[NH:3][CH2:4]2)[CH2:10][CH2:9]1

참가 물질

9

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 126085902-Bromo-1-(2,3-dihydro-1,4-benzodioxin-2-yl)ethan-1-olHCID 129541141-Oxa-3,8-diazaspiro(4.5)decan 2-one

생성물 1

HCID 202966058-[2-(1,4-Benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrochloride

시약·촉매·용매 4

HCID 887Methanol용매2회HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 1.7 g 1-oxa-3,8-diazaspiro[4.5]decan-2-one, 2 g 2-(1-hydroxy-2-bromoethyl)-1,4-benzodioxane [J. Med. Chem., 13, 169 (1970)], 3 ml triethylamine and 5 ml N,N-dimethylformamide is heated at 90° for 18 hours. The mixture is poured into 100 ml water and the resulting mixture stirred for 10 minutes. The stirring is stopped and the aqueous layer decanted. The crude product is filtered through 20 g silica gel with 10% methanol-methylene chloride. Evaporation of the filtrate gives a residue which is taken up in 10 ml methanol. To this solution is added 10 ml of a 3% solution of hydrochloric acid in methanol. Addition of 200 ml of diethyl ether affords a precipitate which is collected by filtration, yielding 1.1 g (mixed erythro and threo) 8-[2-(1,4-benzodioxan-2-yl)-2-hydroxyethyl]-1-oxa-3,8-diazaspiro[4.5]decan-2-one hydrochloride, mp 235°-247° (d).

후처리

  1. temperatureis heated at 90° for 18 hours
  2. customthe aqueous layer decanted
  3. filtrationThe crude product is filtered through 20 g silica gel with 10% methanol-methylene chloride
  4. customEvaporation of the filtrate
  5. customgives a residue which
  6. customaffords a precipitate which
  7. filtrationis collected by filtration

출처 및 근거

ORD 기록
ord-8a38f49d7b9a4d47a450b8bddbd10c53
출처 데이터셋
uspto-grants-1981_01
특허 번호
US04244961

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