Potassium Carbonate → HCID 14873777, compound

HRID 2051514Notes

Reaction equation

HRID 2051514 reaction equation
[O:1]=[C:2]([N:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1)[CH2:3][CH3:4].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.C(OCC)(=O)C>[O:1]=[C:2]([N:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[CH:6]1[CH2:7][CH2:8][N:9]([CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH2:10][CH2:11]1)[CH2:3][CH3:4]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 2593814-(N-Propionylaniline)piperidine

Product 1

HCID 14873777HCID 14873777, compoundYield 53%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[(1-oxopropyl)phenylamino]-piperidine (500 mg, 2.15 mmol), prepared according to the procedure of P. A. J. Janssen et al, U.S. Pat. No. 3,164,600, methyl bromoacetate (0.25 ml, 2.58 mmol), and potassium carbonate (594 mg, 4.3 mmol), in acetonitrile (2.5 ml) is stirred at room temperature for five hours. The reaction mixture is diluted with 1:1 water and ethyl acetate (20 ml total). The phases are separated and the aqueous phase extracted with ethyl acetate (2×) and the combined organics washed with brine, dried over sodium sulfate and then concentrated. The residue is chromatographed on silica gel (95/5 CHCl3 /MeOH) to give 4-[(1-oxopropyl)phenylamino]-1-piperidineacetic acid, methyl ester, as an oil: 348 mg, 53% yield. An equimolar amount of maleic acid in ether is added to a solution of the free base in ethyl acetate to give the maleate salt as a white solid; maleate salt: m.p. 130°-133° C.

Workup

  1. customprepared
  2. customThe phases are separated
  3. extractionthe aqueous phase extracted with ethyl acetate (2×)
  4. washthe combined organics washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on silica gel (95/5 CHCl3 /MeOH)

Sources & evidence

ORD record
ord-79271f20281b4a6a9f2a1aad3d778e65
Source dataset
uspto-grants-1991_05
Patent number
US05019583

Reaction notes

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