Methane → 4-Acetamidopiperidine dihydrochloride

HRID 1290524

Reaction equation

HRID 1290524 reaction equation
[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8](CC2C=CC=CC=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].[ClH:18].[H][H].C>[Pd].CO>[ClH:18].[C:1]([NH:4][CH:5]1[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 297MethaneHCID 313Hydrochloric AcidHCID 12641850N-(1-Benzylpiperidin-4-yl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 114011054-Acetamidopiperidine dihydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

10% w/w Palladium on charcoal (1.5 g) was added to a solution of the product from step i) (10.0 g), 1 molar hydrochloric acid (21.5 ml) and methanol (150 ml) and the mixture hydrogenated at room temperature and pressure until the theoretical amount of hydrogen had been taken up. Charcoal was added, the mixture stirred for 1 hour then filtered through diatomaceous earth and the filtrate evaporated to dryness giving 4-acetylaminopiperidine hydrochloride, 8.64 g, as a sticky foam; NMR (CDCl3 +d6DMSO) δ9.72(1H,b), 9.02(1H,b), 7.40(1H,bd), 3.87(1H,m), 3.30(2H,m), 2.81(2H,m), 1.86(4H,m), 1.80(3H,s); m/e 143 (M+H)+.

Workup

  1. customhydrogenated at room temperature
  2. filtrationthen filtered through diatomaceous earth
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-021e71cb5cff47818031be31b9c5a77c
Source dataset
uspto-grants-1998_05
Patent number
US05750754

Linked notes

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