Sodium Hydroxide → N-[(4-bromophenyl)methyl]-1-morpholino-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

HRID 1068054Notes

Reaction equation

Cl.[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.[OH-].[Na+].[N:13]1([N:19]2[C:28]3[C:23](=[CH:24][C:25]([CH2:29][N:30]4[CH2:35][CH2:34][O:33][CH2:32][CH2:31]4)=[CH:26][CH:27]=3)[C:22](=[O:36])[C:21]([C:37](OCC)=[O:38])=[CH:20]2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>O>[Br:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH:8][C:37]([C:21]2[C:22](=[O:36])[C:23]3[C:28](=[CH:27][CH:26]=[C:25]([CH2:29][N:30]4[CH2:31][CH2:32][O:33][CH2:34][CH2:35]4)[CH:24]=3)[N:19]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[CH:20]=2)=[O:38])=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 190 °C

Procedure

4-Bromobenzylamine hydrochloride (2.22 g) is suspended in water (5 mL) and neutralized with 2N aqueous NaOH (5 mL). The free amine is extracted with dichloromethane (2×25 mL). The organic layers are combined, washed with brine (5 mL), and dried with Na2SO4. The solution is concentrated in vacuo to afford 1.48 g of a clear, colorless oil which is then combined with ethyl 1-(4-morpholinyl)-6-(4-morpholinylmethyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylate (0.48 g) from Preparation No. 56 and heated to 190° C. for 3 hours. The reaction mixture is allowed to cool to room temperature, and the resulting solid is recrystallized in ethyl acetate to afford 0.44 g of the title compound as a white solid.

Workup

extractionThe free amine is extracted with dichloromethane (2×25 mL)
washwashed with brine (5 mL)
dry with materialdried with Na2SO4
concentrationThe solution is concentrated in vacuo
customto afford 1.48 g of a clear, colorless oil which
temperatureto cool to room temperature
customthe resulting solid is recrystallized in ethyl acetate

Sources & evidence

ORD record: ord-e40cb64c7f374a5ea9db5bbe926592f0
Source dataset: uspto-grants-2001_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06248739B1

Reaction notes

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