Methane → HCID 19099559, compound

HRID 1975319Notes

Reaction equation

HRID 1975319 reaction equation
[CH:1]1([CH2:6][CH2:7][C:8](=[O:27])[CH2:9][CH2:10][C:11]2([CH3:26])[CH:16]([CH3:17])[CH2:15][CH2:14][N:13](CC3C=CC=CC=3)[CH:12]2[CH3:25])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C>[Pd].[Pd](Cl)Cl>[CH:1]1([CH2:6][CH2:7][C:8](=[O:27])[CH2:9][CH2:10][C:11]2([CH3:26])[CH:16]([CH3:17])[CH2:15][CH2:14][NH:13][CH:12]2[CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 297MethaneHCID 313Hydrochloric AcidHCID 19099561HCID 19099561, compound

Product 1

HCID 19099559HCID 19099559, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 24290Palladium ChlorideCatalyst

Procedure

A mixture of 1-cyclopentyl-5-[2,3,4-trimethyl-1-(phenylmethyl)-3-piperidinyl]-3-pentanone (6.3 g, 17 mmol), 5 ethanolic HCl (4 mL, 20 mmol) and 10% palladium on carbon (1.2 g) was placed on a Parr hydrogenator at 50 psi for 3 hours, then palladium (II) chloride (0.6 g) and charcoal (1.0 g) were added and the mixture was hydrogenated at 50 psi for 2.5 hours. The catalysts were removed by filtration and the solvent was removed in vacuo. The residue was partitioned between 10% Na2CO3 (100 mL) and ether (2×150 mL), the organic layers were separated and washed with brine (50 mL). The organic layers were dried over Na2SO4 and the solvent was removed in vacuo to afford 4.0 g (84%) of 1-cyclopentyl-5-(2,3,4-trimethyl-3-piperidinyl)-3-pentanone. 2.1 g of the product was used directly in the next step, while the remaining 1.9 g was purified by column chromatography on silica gel eluting with 1-10% triethylamine/ether to afford 1.1 g of the purified product. Treatment of the purified product with 5N ethereal HCl followed by dilution with ether and recrystallization of the solid thus obtained from ethanol/ether afforded 0.8 g of 1-cyclopentyl-5-(2,3,4-trimethyl-3-piperidinyl)-3-pentanone hydrochloride as a white powder, m.p. 127°-128° C.

Workup

  1. waitthe mixture was hydrogenated at 50 psi for 2.5 hours
  2. customThe catalysts were removed by filtration
  3. customthe solvent was removed in vacuo
  4. customThe residue was partitioned between 10% Na2CO3 (100 mL) and ether (2×150 mL)
  5. customthe organic layers were separated
  6. washwashed with brine (50 mL)
  7. dry with materialThe organic layers were dried over Na2SO4
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-b9ec40a683104950baef4e09961eaba5
Source dataset
uspto-grants-1994_02
Patent number
US05286733

Reaction notes

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