Ethyl Acetate → HCID 59457466, compound

HRID 1710786Notes

Reaction equation

HRID 1710786 reaction equation
Cl[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:15]([CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[N:16]=2)=[CH:8][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:35][CH:36]1[CH2:40][CH2:39][CH2:38][NH:37]1.C(OCC)(=O)C>C(#N)C>[CH3:35][CH:36]1[CH2:40][CH2:39][CH2:38][N:37]1[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:15]([CH2:17][N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[N:16]=2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 130032-MethylpyrrolidineHCID 59457472HCID 59457472, compound

Product 1

HCID 59457466HCID 59457466, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
110 °C

Procedure

A solution of ethyl 2-[4-(3-chloropropoxy)phenyl]-4-(piperidin-1-ylmethyl)-1,3-oxazole-5-carboxylate i95 (0.22 g, 0.56 mmol, 1 eq) in acetonitrile (10 ml) is treated with potassium carbonate (0.31 g, 2.24 mmol, 4 eq) and 2-methylpyrrolidine (60 μl, 0.67 mmol, 1.2 eq) and the resulting mixture is stirred at 110° C. overnight. Ethyl acetate is then added and the organic layer is washed with water, dried over magnesium sulfate and concentrated under reduced pressure. Purification over silicagel (eluent: dichloromethane/methanol/ammonia) affords 90 mg of ethyl 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-4-(piperidin-1-ylmethyl)-1,3-oxazole-5-carboxylate i96.

Workup

  1. washthe organic layer is washed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customPurification over silicagel (eluent: dichloromethane/methanol/ammonia)

Sources & evidence

ORD record
ord-4dfd06cf10e84dfd9f60179c777a3e0f
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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