Hydrochloric Acid → HCID 54289162, compound

HRID 2225515Notes

Reaction equation

HRID 2225515 reaction equation
C([O:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11](Cl)=[O:12])=[CH:7][C:6]=1[O:16][CH3:17])(=O)C.[NH:18]1[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=[O:25])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+].Cl>C(OCC)(=O)C>[OH:4][C:5]1[CH:15]=[CH:14][C:8]([CH:9]=[CH:10][C:11]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]([OH:26])=[O:25])[CH2:20][CH2:19]2)=[O:12])=[CH:7][C:6]=1[O:16][CH3:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 37734-Piperidinecarboxylic acidHCID 11430Potassium CarbonateHCID 544680224-Acetoxy-3-methoxycinnamoyl chloride

Product 1

HCID 54289162HCID 54289162, compoundYield 55.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8.1 g of 4-acetoxy-3-methoxycinnamoyl chloride and 15 g of 4-piperidinecarboxylic acid were added to 200 ml of saturated aqueous potassium carbonate. The solution was stirred for 4 hours at room temperature. After reaction, 2N hydrochloric acid was added to the reaction solution, acidifying the solution. 50 ml of ethyl acetate was added to the solution, and the solution was stirred for 1 hour. The crystal precipitated was filtered out and recrystallized from ethyl acetate/hexane, yielding 5.4 g of 1-(4-hydroxy-3-methoxycinnamoyl)piperidine-4-carboxylic acid (a compound of the present invention) as white crystal, which had the following physiochemical properties:

Workup

  1. additionwas added to the reaction solution
  2. stirringthe solution was stirred for 1 hour
  3. customThe crystal precipitated
  4. filtrationwas filtered out
  5. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c341ef89c4654c6cae99e3a3a1e0916b
Source dataset
uspto-grants-1994_09
Patent number
US05344845

Reaction notes

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