4-Hydroxybenzoic Acid → HCID 2371516, compound

HRID 1105794Notes

Reaction equation

HRID 1105794 reaction equation
C(#N)C.Cl[CH2:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)=[O:7].[OH:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=1>C(N(CC)CC)C>[OH:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([O:21][CH2:5][C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)=[O:7])=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1354-Hydroxybenzoic AcidHCID 6342AcetonitrileHCID 2223122-Chloro-1-piperidine-1-yl-ethanone

Product 1

HCID 2371516HCID 2371516, compoundYield 83.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 100 ml of acetonitrile were added 7.75 g of N-(α-chloroacetyl)piperidine, 5.0 g of 4-hydroxybenzoic acid and 4.3 g (5.9 ml) of triethylamine, and the mixture was refluxed with heating for 2 hours. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. To the residue was added ice-water, and precipitated crystals were recrystallized from water to give 8.0 g of the title compound. Melting point: 160°-164° C.

Workup

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 2 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionTo the residue was added ice-water
  6. customprecipitated crystals
  7. customwere recrystallized from water

Sources & evidence

ORD record
ord-86c6add9d48e4d3a89318834ca37cd97
Source dataset
uspto-grants-1982_01
Patent number
US04310533

Reaction notes

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