Hydrogen chloride-ethyl acetate → HCID 66751341, compound

HRID 535021Notes

Reaction equation

HRID 535021 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 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 66751357HCID 66751357, compound

Product 1

HCID 66751341HCID 66751341, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of tert-butyl 4-[(4-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}phenoxy)methyl]piperidine-1-carboxylate (1.5 g, 2.8 mmol) and 4 M hydrochloric acid-ethyl acetate solution (20 mL) in ethyl acetate (100 mL) and methanol (100 mL) was stirred at room temperature for 16 h. Solvent was removed in vacuo and 1 M sodium hydroxide solution was added to the mixture. 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 obtain a solid (1.1 g, 90%).

Workup

  1. customSolvent was removed in vacuo and 1 M sodium hydroxide solution
  2. additionwas added to the mixture
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-63bf5c0fb7ab46d5809d0efb86f839c3
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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