Water → 1-(Morpholin-4-yl)-3-[2-(piperidin-4-yloxy)pyridin-5-yl]-prop-2-ene-1-one
Reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([CH:21]=[CH:22][C:23]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)=[O:24])=[CH:17][N:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.O>ClCCl>[N:25]1([C:23](=[O:24])[CH:22]=[CH:21][C:18]2[CH:19]=[CH:20][C:15]([O:14][CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[N:16][CH:17]=2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-[2-(1-t-Butyloxycarbonyl piperidin-4-yloxy)pyridin-5-yl]-1-(morpholin-4-yl)prop-2-ene-1-one (0.7 grams, 0.0016 moles) in dichloromethane (20 mL) was treated with trifluoroacetic acid (1.3 mL, 0.016 moles) at room temperature. The reaction mass was stirred for 6 hours at room temperature. The progress of the reaction was monitored by thin layer chromatography. After completion of reaction, the reaction mass was poured on to chilled water (30 mL) and basified with 40% lye solution (pH˜9). The layers were separated and the aqueous layer was further extracted with dichloromethane (2×20 mL). The combined organic phase was washed with water (30 mL), brine solution (30 mL) and dried over sodium sulphate. The organic phase was concentrated on rotavacuum to afford the title compound (0.48 grams).
Workup
- customAfter completion of reaction
- additionthe reaction mass was poured on
- customThe layers were separated
- extractionthe aqueous layer was further extracted with dichloromethane (2×20 mL)
- washThe combined organic phase was washed with water (30 mL), brine solution (30 mL)
- dry with materialdried over sodium sulphate
- concentrationThe organic phase was concentrated on rotavacuum
Sources & evidence
- ORD record
- ord-c70641309e454a4daf2c2ff44da34ac7
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09328092B2
Reaction notes
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