Ethyl Acetate → HCID 66751341, compound

HRID 534904Notes

Reaction equation

HRID 534904 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:39]=[CH:38][C:22]([O:23][CH2:24][CH:25]3[CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Cl.C(OCC)(=O)C.C(OCC)(=O)C>CO>[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:23][CH2:24][CH:25]3[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]3)=[CH:38][CH:39]=2)=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21866389Hydrogen chloride-ethyl acetateHCID 66751357HCID 66751357, compound

Product 1

HCID 66751341HCID 66751341, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of tert-butyl 4-[(4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}phenoxy)methyl]piperidine-1-carboxylate obtained in Example 37 (1.5 g), 4 M hydrochloric acid-ethyl acetate solution (20 mL), ethyl acetate (100 mL), and methanol (100 mL) was stirred at room temperature for 16 h. The solvent was evaporated. 1 M sodium hydroxide solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to provide the title compound (1.1 g, 90%) as crystals.

Workup

  1. customThe solvent was evaporated
  2. addition1 M sodium hydroxide solution was added to the reaction solution
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-342e37bf1b90446cb95ca24de3adaff2
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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