Formic Acid → HCID 21955288, compound

HRID 2212999Notes

Reaction equation

HRID 2212999 reaction equation
[CH3:1][N:2]([CH3:23])[C:3]1([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:8][CH2:7][N:6](CC2C=CC=CC=2)[CH2:5][CH2:4]1.C(O)=O.C([O-])=O.[NH4+]>[Pd].CO>[CH3:23][N:2]([CH3:1])[C:3]1([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:4][CH2:5][NH:6][CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 284Formic AcidHCID 2723923Ammonium formateHCID 21955361HCID 21955361, compound

Product 1

HCID 21955288HCID 21955288, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of palladium on carbon (10%, 2 g) was added to a solution of 4-(dimethylamino)-1,4-bis(phenylmethyl)piperidine (Description 13, 4.62 g, 15 mmol) and formic acid (90%, 1.4 mL) in methanol (100 mL). Ammonium formate (4.73 g, 75 mmol) was added and the mixture was stirred at room temperature for 20 hours. The mixture was filtered, washing with methanol, and the solvent was evaporated under reduced pressure. Ether (40 mL) was added and the mixture was extracted with hydrochloric acid (1M, 3×40 mL). The combined aqueous layers were washed with ether (40 mL), adjusted to pH 12.0 with aqueous sodium hydroxide (4M) and extracted with dichloromethane (3×40 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was triturated with hexane (20 mL) and the solid was collected and dried in vacuo to give the the title compound as a colorless solid (2.20 g, 67%). m/z (ES+) 219 (M+1).

Workup

  1. filtrationThe mixture was filtered
  2. washwashing with methanol
  3. customthe solvent was evaporated under reduced pressure
  4. additionEther (40 mL) was added
  5. extractionthe mixture was extracted with hydrochloric acid (1M, 3×40 mL)
  6. washThe combined aqueous layers were washed with ether (40 mL)
  7. extractionextracted with dichloromethane (3×40 mL)
  8. dry with materialThe combined organic fractions were dried (MgSO4)
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was triturated with hexane (20 mL)
  11. customthe solid was collected
  12. customdried in vacuo

Sources & evidence

ORD record
ord-046b164bdffd47dea276ef8fe1d398c4
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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