Water → HCID 66751222, compound

HRID 535022Notes

Reaction equation

HRID 535022 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH:27]3[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]3)=[CH:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:34](=[O:39])[C:35]([O:37][CH3:38])=[O:36].C(N(CC)CC)C.O>O1CCCC1>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][CH:27]3[CH2:32][CH2:31][N:30]([C:34](=[O:39])[C:35]([O:37][CH3:38])=[O:36])[CH2:29][CH2:28]3)=[CH:23][CH:24]=2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 79846Methyl chloroglyoxylateHCID 66751341HCID 66751341, compound

Product 1

HCID 66751222HCID 66751222, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-tert-butylphenyl)-4-{[4-(piperidin-4-ylmethoxy)phenyl]carbonyl}piperazine (0.44 g, 1.01 mmol), methyl chloro(oxo)acetate (0.153 g, 1.25 mmol) and triethylamine (0.279 mL, 2.0 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 16 h. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford a solid (0.527 g, 100%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-37fc49864d8e43fe95237d6414c97a58
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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