Formic Acid → Biphenyl-2-ylcarbamic Acid Piperidin-4-yl Ester

HRID 2121005Notes

Reaction equation

HRID 2121005 reaction equation
[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:23])[O:9][CH:10]1[CH2:15][CH2:14][N:13](CC2C=CC=CC=2)[CH2:12][CH2:11]1.C(O)=O>CO.[Pd]>[C:1]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:23])[O:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 105003691-benzyl-4-piperidyl N-(2-biphenylyl)carbamate

Product 1

HCID 10851461Biphenyl-2-ylcarbamic Acid Piperidin-4-yl EsterYield 69.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-Benzyl-4-piperidyl N-(2-biphenylyl)carbamate (12.5 g, 32.3 mmol) was dissolved in anhydrous methanol (150 mL) and formic acid (25 mL, 660 mmol) and the solution was flushed with gaseous nitrogen for 15 min. 10% Palladium on carbon (3 g) was added and the reaction mixture was stirred under nitrogen atmosphere. After 18 h, the reaction mixture was filtered through CeliteR and the filtrate was concentrated to give a yellow solid. The solid was partitioned between 0.1 N hydrochloric acid (300 mL) and diethyl ethr (300 mL). The aqueous layer was washed with diethyl ether and then basified with 1 N sodium hydroxide solution to pH 12. A white solid precipitated out which was extracted into ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and evaporated to dryness to give 4-piperidyl N-(2-biphenylyl)carbamate as a colorless solid (6.63 g, 69%). MS=296.9 MH+.

Workup

  1. filtrationthe reaction mixture was filtered through CeliteR
  2. concentrationthe filtrate was concentrated
  3. customto give a yellow solid
  4. customThe solid was partitioned between 0.1 N hydrochloric acid (300 mL) and diethyl ethr (300 mL)
  5. washThe aqueous layer was washed with diethyl ether
  6. customA white solid precipitated out which
  7. extractionwas extracted into ethyl acetate
  8. dry with materialThe ethyl acetate layer was dried over magnesium sulfate
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-d38d16c90c6d4da287da2f87412383f4
Source dataset
uspto-grants-2004_02
Patent number
US06693202B1

Reaction notes

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