Water → 3-[4-(Piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-one

HRID 520814Notes

Reaction equation

HRID 520814 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][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.O>ClCCl>[NH:8]1[CH2:9][CH2:10][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][CH:16]=2)[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 900429883-[4-(1-t-Butyloxycarbonyl piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-one

Product 1

HCID 900427143-[4-(Piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-oneYield 94.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-[4-(1-t-Butyloxycarbonyl piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-one (29.8 grams, 0.071 moles) in dichloromethane (400 mL) was treated with trifluoroacetic acid (55.6 mL, 0.726 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 the reaction, the reaction mass was poured on to chilled water (500 mL) and basified with 40% lye solution (pH˜9). The layers were separated and the aqueous layer was extracted with dichloromethane (2×200 mL) and the combined organic phase was washed with water (150 mL), brine solution (150 mL) and dried over sodium sulphate. The organic phase was concentrated on rotavacuum to afford the title compound (21.2 grams).

Workup

  1. customAfter completion of the reaction
  2. additionthe reaction mass was poured on
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×200 mL)
  5. washthe combined organic phase was washed with water (150 mL), brine solution (150 mL)
  6. dry with materialdried over sodium sulphate
  7. concentrationThe organic phase was concentrated on rotavacuum

Sources & evidence

ORD record
ord-576ec1abebcd47cf882fde42258ea597
Source dataset
uspto-grants-2016_05
Patent number
US09328092B2

Reaction notes

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