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

HRID 1389478Notes

Reaction equation

HRID 1389478 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].[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

Participants

9

Reactant 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

Product 1

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

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8a38f49d7b9a4d47a450b8bddbd10c53
Source dataset
uspto-grants-1981_01
Patent number
US04244961

Reaction notes

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