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

HRID 272793Notes

Reaction equation

HRID 272793 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 Celite® 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 Celite®
  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-29e6588109d044789fafa6c4cc2626e6
Source dataset
uspto-grants-2008_11
Patent number
US07456203B2

Reaction notes

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