Bicarbonate Ion → HCID 21192569, compound

HRID 1068038Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]([CH:22]=[C:23]([C:29]([O:31]CC)=O)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.C(=O)(O)[O-]>ClCCl>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:9]3[C:10](=[CH:11][C:12]([CH2:15][N:16]4[CH2:17][CH2:18][O:19][CH2:20][CH2:21]4)=[CH:13][CH:14]=3)[C:29](=[O:31])[C:23]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:22]2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 130 °C

Procedure

A flask containing diethyl 2-{[(1-methyl-4-piperidinyl)-4-(4-morpholinylmethyl)anilino]methylene}malonate (0.36 g) is treated with polyphosphoric acid (1.8 g). The reaction mixture is heated to 130° C. under a flow of nitrogen gas. After 4 hours the reaction is cooled to room temperature. The reaction mixture is carefully added to a vigorously stirred mixture of dichloromethane and saturated aqueous bicarbonate. The layers are separated and the basic aqueous layer is extracted with three additional portions of dichloromethane. The combined organic layers are washed with brine, dried over sodium sulfate and concentrated under reduced pressure to afford 0.32 g of crude ethyl 1-(1-methyl-4-piperidinyl)-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate as a tan solid.

Workup

temperatureAfter 4 hours the reaction is cooled to room temperature
customThe layers are separated
extractionthe basic aqueous layer is extracted with three additional portions of dichloromethane
washThe combined organic layers are washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-004d7f3a0d2a437b80d12fc37c29b2ae
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248739B1

Reaction notes

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