Hydrochloric Acid → 92329-61-8

HRID 989887Notes

Reaction equation

HRID 989887 reaction equation
CC(OC([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=O)(C)C.[H][H].[ClH:25]>CO.[Rh]>[ClH:25].[CH:17]1([C:11]2([C:14]([OH:16])=[O:15])[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 7369171-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 6984437692329-61-8

Reagents, catalysts & solvents 2

HCID 23948RhodiumCatalystHCID 887MethanolSolvent

Procedure

4-Phenyl-1,4-piperidinedicarboxylic acid 1-(1,1-dimethylethyl) ester (8-2) (202 g, 0.662 mol) was dissolved in 1700 mL of 10% HCl in methanol and rhodium on alumina (25 g) was added. The mixture was placed on a high pressure hydrogenator using 1500 psi of hydrogen at 100° C. for 17 h. The resulting mixture was filtered through Celite using methanol to rinse and concentrated. The resulting solid was triturated with diethyl ether and filtered to afford title compound 8-3 as an off-white solid.

Workup

  1. customat 100° C.
  2. customfor 17 h
  3. filtrationThe resulting mixture was filtered through Celite
  4. washto rinse
  5. concentrationconcentrated
  6. customThe resulting solid was triturated with diethyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-49b4e56047d4497da7f4e86c1adb2340
Source dataset
uspto-grants-2002_10
Patent number
US06458790B2

Reaction notes

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