Potassium Carbonate → 4-(2-{4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}-2-oxoethyl)morpholine-3,5-dione

HRID 538696Notes

Reaction equation

HRID 538696 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[C:15](=[O:16])[C:14]([CH3:18])([CH3:17])[C:13]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH3:28])[CH:20]=3)=[N:12]2)[CH2:7][CH2:6]1)=[O:4].[NH:29]1[C:34](=[O:35])[CH2:33][O:32][CH2:31][C:30]1=[O:36].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:28][O:27][C:21]1[CH:20]=[C:19]([C:13]2[C:14]([CH3:18])([CH3:17])[C:15](=[O:16])[N:11]([CH:8]3[CH2:7][CH2:6][N:5]([C:3](=[O:4])[CH2:2][N:29]4[C:34](=[O:35])[CH2:33][O:32][CH2:31][C:30]4=[O:36])[CH2:10][CH2:9]3)[N:12]=2)[CH:24]=[CH:23][C:22]=1[O:25][CH3:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 364836Morpholine-3,5-dioneHCID 666166092-[1-(chloroacetyl)piperidin-4-yl]-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one2×

Product 1

HCID 251158444-(2-{4-[3-(3,4-dimethoxyphenyl)-4,4-dimethyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl]piperidin-1-yl}-2-oxoethyl)morpholine-3,5-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g 2-[1-(chloroacetyl)piperidin-4-yl]-5-(3,4-dimethoxyphenyl)-4,4-dimethyl-2,4-dihydro-3H-pyrazol-3-one (compound A1), 0.5 g morpholine-3,5-dione and 1.0 g K2CO3 in 20 ml of DMF is heated for 17 h at 80-100° C. The DMF is removed in vacuo and the residue dissolved in 70 ml of DCM, washed four times with 30 ml of water and 20 ml of 0.5 M H2SO4. The DCM layer is dried over MgSO4 and concentrated in vacuo. The title product is crystallized from diethyl ether.

Workup

  1. customThe DMF is removed in vacuo
  2. dissolutionthe residue dissolved in 70 ml of DCM
  3. washwashed four times with 30 ml of water and 20 ml of 0.5 M H2SO4
  4. dry with materialThe DCM layer is dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe title product is crystallized from diethyl ether

Sources & evidence

ORD record
ord-afa53fa540e14764851c141eebdbaf6c
Source dataset
uspto-grants-2014_10
Patent number
US08865745B2

Reaction notes

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