Hydrochloric Acid → 1-(2-Amino-4-fluorophenyl)piperidine-3-carboxamide hydrochloride

HRID 722233Notes

Reaction equation

HRID 722233 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([NH2:16])=[O:15])[CH2:9]2)=[C:4]([N+:17]([O-])=O)[CH:3]=1.[H][H].[ClH:22]>C1COCC1.C(OCC)(=O)C.[Pd]>[ClH:22].[NH2:17][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]([NH2:16])=[O:15])[CH2:9]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 218839121-(4-Fluoro-2-nitrophenyl)piperidine-3-carboxamideHCID 178418361HCID 178418361, compound

Product 1

HCID 218838991-(2-Amino-4-fluorophenyl)piperidine-3-carboxamide hydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 2.67 g of 1-(4-fluoro-2-nitrophenyl)piperidine-3-carboxamide in 100 ml of THF was admixed with 260 mg of Pd/C. This mixture was hydrogenated in a shaking vessel at atmospheric pressure until the theoretical amount of hydrogen had been taken up. The mixture is then acidified with hydrogen chloride dissolved in ethyl acetate, the solid is filtered off with suction and washed with methanol, and the filtrate is concentrated under reduced pressure. The residue is triturated with tert-butyl methyl ether and the solid is filtered off with suction and dried under reduced pressure.

Workup

  1. filtrationthe solid is filtered off with suction
  2. washwashed with methanol
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is triturated with tert-butyl methyl ether
  5. filtrationthe solid is filtered off with suction
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-460b37341dca48ddbd1f94fc12ac05d9
Source dataset
uspto-grants-2006_11
Patent number
US07138414B2

Reaction notes

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