Hydrochloric Acid → 1-Benzoyl-4-benzylpiperidine-4-carboxylic acid

HRID 1591151Notes

Reaction equation

HRID 1591151 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][C:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]([O:17]CC)=[O:16])[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].Cl>CS(C)=O>[C:1]([N:9]1[CH2:10][CH2:11][C:12]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]([OH:17])=[O:16])[CH2:13][CH2:14]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10545888Ethyl-1-benzoyl-4-(phenylmethyl)-4-piperidinecarboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 222406641-Benzoyl-4-benzylpiperidine-4-carboxylic acidYield 78.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 10.7 g (26 mmoles) crude ethyl 1-benzoyl-4-(phenylmethyl)-4-piperidinecarboxylate was added a solution of 14.6 g (130 mmoles) potassium tert-butoxide in 130 ml dimethyl sulfoxide. The resulting purple solution was stirred 2 hours to give a dark orange solution. The solution was poured into 500 ml rapidly stirred ice-water and acidified with 12 ml concentrated hydrochloric acid. The resulting white precipitate was filtered off, washed with 3×20 ml cold water, then dissolved in 200 ml ether. The ether solution was washed with 3×20 ml water, and brine, dried, and the solvent was removed in vacuo to give a pale yellow foam. The product was recrystallized from ether to give 6.63 g (75%) product, m.p. 183°-189° C.

Workup

  1. customto give a dark orange solution
  2. filtrationThe resulting white precipitate was filtered off
  3. washwashed with 3×20 ml cold water
  4. dissolutiondissolved in 200 ml ether
  5. washThe ether solution was washed with 3×20 ml water, and brine
  6. customdried
  7. customthe solvent was removed in vacuo
  8. customto give a pale yellow foam
  9. customThe product was recrystallized from ether

Sources & evidence

ORD record
ord-f4bf7eedb16a4b1987a91f4f85ff9c44
Source dataset
uspto-grants-1993_04
Patent number
US05206240

Reaction notes

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