Formic Acid → HCID 10638702, compound

HRID 272797Notes

Reaction equation

HRID 272797 reaction equation
[CH:1]([NH:14][C:15](=[O:30])[O:16][CH:17]1[CH2:22][CH2:21][N:20](CC2C=CC=CC=2)[CH2:19][CH2:18]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=O>CO>[CH:1]([NH:14][C:15](=[O:30])[O:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 107871791-benzyl-4-piperidyl benzhydrylcarbamate

Product 1

HCID 10638702HCID 10638702, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-benzylpiperidin-4-yl benzhydrylcarbamate (46.3 g, 119 mmol) and formic acid (100 mL) in methanol (600 mL) was stirred at room temperature and nitrogen was bubbled through the reaction mixture for about 20 min. The reaction mixture was then transferred to a slurry of 10% palladium on carbon in water (75 mL.) via a thick needle and stirring was continued overnight. The reaction mixture was filtered, concentrated under reduced pressure, and dried under high vacuum overnight. The residue was then diluted with ethyl acetate and washed with satd. NaHCO3 (aq.). The organic layer was separated, concentrated under reduced pressure, diluted with 0.1N HCl (pH3) and ether. The ether layer was separated and the aqueous layer was basified with 1N NaOH (aq) to pH13-14. to give a solid which was filtered to yield piperidin-4-yl benzhydrylcarbamate.

Workup

  1. customnitrogen was bubbled through the reaction mixture for about 20 min
  2. stirringstirring
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customdried under high vacuum overnight
  6. additionThe residue was then diluted with ethyl acetate
  7. washwashed with satd
  8. customThe organic layer was separated
  9. concentrationconcentrated under reduced pressure
  10. additiondiluted with 0.1N HCl (pH3) and ether
  11. customThe ether layer was separated
  12. customto give a solid which
  13. filtrationwas filtered

Sources & evidence

ORD record
ord-b48675da97cf47519cbac2b990313762
Source dataset
uspto-grants-2008_11
Patent number
US07456203B2

Reaction notes

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