Ammonium formate → 2-{4-[4-Amino-3-(propan-2-yloxy)phenyl]piperidin-1-yl}ethanol

HRID 518868Notes

Reaction equation

HRID 518868 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][OH:18])[CH2:14][CH:15]=2)=[CH:6][C:5]=1[O:19][CH:20]([CH3:22])[CH3:21])([O-])=O.C([O-])=O.[NH4+]>C(O)C.ClCCl.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][OH:18])[CH2:14][CH2:15]2)=[CH:6][C:5]=1[O:19][CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 866980212-{4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridin-1(2H)-yl}ethanol

Product 1

HCID 683600452-{4-[4-Amino-3-(propan-2-yloxy)phenyl]piperidin-1-yl}ethanolYield 90.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 150 mg of 10% palladium-on-carbon and 400 mg of 2-{4-[4-nitro-3-(propan-2-yloxy)phenyl]-3,6-dihydropyridin-1(2H)-yl}ethanol in 15 ml of ethanol is heated at 80° C. with stirring. 1.25 g of ammonium formate are then added in two portions. After stirring at 80° C. for 1 h, the mixture is allowed to return to ambient temperature and is filtered on Clarcel. The Clarcel is rinsed with 200 ml of ethanol and the filtrate is concentrated under vacuum, so as to obtain a residue which is solubilised in 150 ml of dichloromethane. The organic phase is washed three times with 70 ml of a saturated potassium carbonate solution, and the aqueous phase is extracted twice with 100 ml of dichloromethane. The combined organic phases are dried over magnesium sulfate, filtered and concentrated under vacuum, so as to obtain 330 mg of 2-{4-[4-amino-3-(propan-2-yloxy)phenyl]piperidin-1-yl}ethanol used without further purification.

Workup

  1. stirringAfter stirring at 80° C. for 1 h
  2. customto return to ambient temperature
  3. filtrationis filtered on Clarcel
  4. washThe Clarcel is rinsed with 200 ml of ethanol
  5. concentrationthe filtrate is concentrated under vacuum
  6. customso as to obtain a residue which
  7. washThe organic phase is washed three times with 70 ml of a saturated potassium carbonate solution
  8. extractionthe aqueous phase is extracted twice with 100 ml of dichloromethane
  9. dry with materialThe combined organic phases are dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-3c31278b78b54634b06ecf573cacb6a8
Source dataset
uspto-grants-2015_08
Patent number
US09115140B2

Reaction notes

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