Methane → 4-Acetamidopiperidine dihydrochloride

HRID 864837

Reaction equation

HRID 864837 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-d40ed0e0050a4124b2661c20b7334150
Source dataset
uspto-grants-1996_10
Patent number
US05563141

Linked notes

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