Water → 9-[2-(1,4-Benzodioxan-2-yl)ethyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one
Reaction equation
[O:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][NH:4][C:3](=[O:12])[CH2:2]1.[O:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH:14]1[CH2:23][CH2:24]Br.O>CN(C)C=O.C(N(CC)CC)C>[O:13]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[O:16][CH2:15][CH:14]1[CH2:23][CH2:24][N:9]1[CH2:8][CH2:7][C:6]2([O:1][CH2:2][C:3](=[O:12])[NH:4][CH2:5]2)[CH2:11][CH2:10]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 1-oxa-4,9-diazaspiro[5.5]undecan-3-one (2.5 g.) and 3.0 g. of 2-(1,4-benzodioxan-2-yl)ethyl bromide in 40 ml of dimethylformamide and 10 ml of triethylamine was heated to 70° C. for 3 hours. The mixture was poured into water, extracted with methylene chloride, and the methylene chloride was extracted with aqueous HCl. The aqueous extract was made basic with ammonium hydroxide and extracted with methylene chloride and the methylene chloride layer was evaporated to give 9-[2-(1,4-benzodioxan-2-yl)ethyl]-1-oxa-4,9-diazaspiro[5.5]undecan-3-one, m.p. 139°-140° C. The base was converted to the HCl salt of 9-[2-(1,4-benzodioxan-2-yl)ethyl]-1-oxa-4,9-diazaspiro-[5.5]undecan-3-one by dissolution in methanolic HCl and precipitation with ether, m.p. 225°-227° C.
Workup
- extractionextracted with methylene chloride
- extractionthe methylene chloride was extracted with aqueous HCl
- extractionThe aqueous extract
- extractionextracted with methylene chloride
- customthe methylene chloride layer was evaporated
Sources & evidence
- ORD record
- ord-5554d8e1dea74377a08f171b708ed2ae
- Source dataset
- uspto-grants-1982_10
- Patent number
- US04353901
Reaction notes
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