Hydrochloric Acid → 1-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid

HRID 991499Notes

Reaction equation

HRID 991499 reaction equation
[C:1]1([C:7]2([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]1([CH3:26])[CH:21]=CC(S(O)(=O)=O)=C[CH:17]=1.[C:27]([O-])([O-:29])=[O:28].[K+].[K+].Cl>O1CCOCC1.CCOCC.O>[C:16]([O:29][C:27]([N:10]1[CH2:9][CH2:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:13]([OH:15])=[O:14])[CH2:12][CH2:11]1)=[O:28])([CH3:26])([CH3:21])[CH3:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 192594-Phenylpiperidine-4-carboxylic acid, compound with toluene-p-sulphonic acid

Product 1

HCID 7369171-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
60 °C

Procedure

Place 100 g of 4-phenylpiperidine-4-carboxylic acid and p-toluenesulphonic acid in 800 ml of dioxane, add 150 ml of water and 109.7 g of K2CO3. Heat to 60° C. then add, drop by drop, 60.7 g of (Boc)20 in 100 ml of dioxane. Leave for 4 hours with stirring at 60° C. then heat under reflux for 1 hour. Evaporate to dryness, take up the solid formed in water, acidify to a pH of 3 by the addition of 2 N HCl, then add ether. Filter the crystals formed, wash them in water then in ether. Evaporate the etherified filtrate to dryness, take up the residue in ether and filter the crystals formed and add to those already obtained in order to dry them. 71 g of the desired compound are obtained.

Workup

  1. additionthen add
  2. customLeave for 4 hours
  3. temperaturethen heat
  4. temperatureunder reflux for 1 hour
  5. customEvaporate to dryness
  6. customformed in water
  7. filtrationFilter the crystals
  8. customformed
  9. washwash them in water
  10. customEvaporate the etherified filtrate to dryness
  11. filtrationfilter the crystals
  12. customformed
  13. additionadd to
  14. customthose already obtained in order
  15. customto dry them

Sources & evidence

ORD record
ord-3799ff22e5c5452aab8dc03b0a5fe9b3
Source dataset
uspto-grants-2002_10
Patent number
US06465489B1

Reaction notes

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