Fumaric Acid → 3-[4-(1-Cyclobutyl piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-one fumarate salt

HRID 520818Notes

Reaction equation

HRID 520818 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:17]=[CH:16][C:15]([CH:18]=[CH:19][C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])=[CH:14][CH:13]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32]>CO>[C:28]([OH:35])(=[O:34])/[CH:29]=[CH:30]/[C:31]([OH:33])=[O:32].[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[CH:13]=[CH:14][C:15]([CH:18]=[CH:19][C:20]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[O:21])=[CH:16][CH:17]=3)[CH2:7][CH2:6]2)[CH2:2][CH2:3][CH2:4]1

Participants

4

Reactant 2

HCID 444972Fumaric AcidHCID 900417633-[4-(1-Cyclobutyl piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-one

Product 1

HCID 900424743-[4-(1-Cyclobutyl piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-one fumarate saltYield 96.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 3-[4-(1-Cyclobutyl piperidin-4-yloxy)phenyl]-1-(morpholin-4-yl)prop-2-ene-1-one (23.52 grams, 0.063 moles) in methanol (300 mL) was added a solution of fumaric acid (7.32 grams, 0.063 moles) in 30 mL methanol. The clear mass, thus obtained, was further stirred for 2-3 hours at room temperature. The solvent was evaporated to afford a solid mass. The solid mass was triturated with diethyl ether (3×100 mL) and dried under reduced pressure to obtain the title compound (29.54 grams).

Workup

  1. customThe clear mass, thus obtained
  2. customThe solvent was evaporated
  3. customto afford a solid mass
  4. customThe solid mass was triturated with diethyl ether (3×100 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-96ac3a223fca4c62bc3077efedfe5c92
Source dataset
uspto-grants-2016_05
Patent number
US09328092B2

Reaction notes

Loading…