Ethyl Acetate → HCID 19029356, compound

HRID 2256295Notes

Reaction equation

HRID 2256295 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH3:26])[C:9](=[O:25])[CH2:10][CH:11]([CH2:18][CH2:19]OS(C)(=O)=O)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[C:27]([NH:30][C:31]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)(=[O:29])[CH3:28].C(N(C(C)C)C(C)C)C.CCOC(C)=O>CN(C=O)C.O>[C:27]([NH:30][C:31]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:32][CH2:33][N:34]([CH2:19][CH2:18][CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][C:9]([N:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH3:26])=[O:25])[CH2:35][CH2:36]1)(=[O:29])[CH3:28]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 15886675N-(4-Phenylpiperidin-4-yl)acetamideHCID 19029315HCID 19029315, compound

Product 1

HCID 19029356HCID 19029356, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-(4-Chlorophenyl)-beta-(2-methanesulfonyloxyethyl)-N-methyl-benzenepropanamide (2.0 g) in DMF (10 mL) was treated with 4-acetylamino-4-phenylpiperidine hydrochlorode (3.21 g) and ethyl-N,N-diisopropylamine (2.48 g) and the mixture heated at 80° C. for 2 hours. The cooled reaction mixture was diluted the EtOAc (50 mL) and water (50 mL) and the aqueous phase removed. The aqueous layer was extracted with EtOAc (2×50 mL) and the combined organic extracts, washed with water (50 mL), dried over MgSO4, filtered and concentrated under reduced pressure to give an oil. Silica gel chromatography eluting with 10% MeOH:CHaCl2 gave the title compound (0.29 g). Mass spectrum (FAB): 518.3.

Workup

  1. customThe cooled reaction mixture
  2. customthe aqueous phase removed
  3. extractionThe aqueous layer was extracted with EtOAc (2×50 mL)
  4. washthe combined organic extracts, washed with water (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give an oil
  9. washSilica gel chromatography eluting with 10% MeOH

Sources & evidence

ORD record
ord-bb16d805d6694a87b316e00126cde9cf
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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