Water → HCID 17795970, compound

HRID 2187073Notes

Reaction equation

[O:1]=[C:2]1[N:11]([CH2:12][CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][CH2:16]2)[C:10](=[O:35])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.C(=O)([O-])[O-].[K+].[K+].[C:42]([O:46][CH3:47])(=[O:45])[CH:43]=[CH2:44].O>CN(C)C=O>[O:1]=[C:2]1[N:11]([CH2:12][CH2:13][CH2:14][N:15]2[CH2:16][CH2:17][CH:18]([O:21][CH:22]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:19][CH2:20]2)[C:10](=[O:35])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[CH2:44][CH2:43][C:42]([O:46][CH3:47])=[O:45]

Participants

Conditions

Temperature: 120 °C

Procedure

2,4-Dioxo-3-[3-(4-diphenylmethoxypiperidino)propyl]-1,2,3,4-tetrahydroquinazoline (3.50 g) obtained in Example 79 and potassium carbonate (1.24 g) were suspended in N,N-dimethylformamide (50.0 ml), and then methyl acrylate (1.01 ml) was added. The reaction mixture was stirred at 120° C. for 20 hours, poured onto an iced water, and then extracted with ethyl acetate. After the extract was washed with water and dried (Na2SO4), the solvent was distilled off under reduced pressure. The residue was subjected to a column chromatography on a silica gel eluting with n-hexane-ethyl acetate (3:1, v/v) to give the title compound (1.73 g, 42%) as a crystal. This product was used in the next reaction without further purification.

Workup

extractionextracted with ethyl acetate
washAfter the extract was washed with water
dry with materialdried (Na2SO4)
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-2fa8dd3f8bf442d0ace5e6cf2cbc9a44
Source dataset: uspto-grants-2002_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06407116B1

Reaction notes

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