Water → HCID 86745423, compound

HRID 1091016Notes

Reaction equation

[C:1]1([N:7]2[C:11]3([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:19][CH:20]1[CH2:25][N:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23]2[CH:32]=[CH:33][CH:34]=[CH:35][C:22]=2[O:21]1.O>CN(C)C=O>[C:1]1([N:7]2[C:11]3([CH2:12][CH2:13][N:14]([C:20]4([CH3:19])[CH2:25][N:24]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:23]5[CH:32]=[CH:33][CH:34]=[CH:35][C:22]=5[O:21]4)[CH2:15][CH2:16]3)[C:10](=[O:17])[NH:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one (2.03 g; 8.8 mmol) is added to a stirred solution of 2-chloromethyl-4-phenyl-2,3-dihydro-4H-1,4-benzoxazine (1.29 g; 4 mmol) in dimethylformamide (20 ml). The reacting mixture is heated at 90° C. for 8 hours. After cooling, water (100 ml) is added and the product is extracted twice with ethyl acetate (80 ml). The organic layer is washed twice with water (30 ml) and dried over anhydrous sodium sulphate. The solid residue, obtained after evaporation of the solvent under reduced pressure, is purified by flash column chromatography on silica gel by using hexane/acetone=9/1 as eluant, thus obtaining 0.7 g of pure 2-(1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one-8-yl)-methyl-4-phenyl-2,3-dihydro-4H-1,4-benzoxazine, yield 37%; m.p. 191°-193° C.

Workup

temperatureAfter cooling
extractionthe product is extracted twice with ethyl acetate (80 ml)
washThe organic layer is washed twice with water (30 ml)
dry with materialdried over anhydrous sodium sulphate
customThe solid residue, obtained
customafter evaporation of the solvent under reduced pressure
customis purified by flash column chromatography on silica gel

Sources & evidence

ORD record: ord-97ad6e599cc04a08b7ba83244d367227
Source dataset: uspto-grants-1992_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05084454

Reaction notes

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