HCID 178483794, compound → HCID 178484858, compound

HRID 2118232Notes

Reaction equation

HRID 2118232 reaction equation
C(O[C:9](=O)[N:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]([O:18][CH2:19][C:20](=[O:28])[N:21]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH3:22])[CH2:14][CH2:13]1)C)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH3:27][N:25]([CH3:26])[CH2:24][CH2:23][N:21]([CH3:22])[C:20](=[O:28])[CH2:19][O:18][C@H:15]1[CH2:14][CH2:13][C@H:12]([NH:10][CH3:9])[CH2:17][CH2:16]1

Participants

4

Reactant 1

HCID 178483794HCID 178483794, compound

Product 1

HCID 178484858HCID 178484858, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

6.24 g (13.38 mmol) of trans-(4-{[(2-dimethylamino-ethyl)-methyl-carbamoyl]-methoxy}-cyclohexyl)-methyl-carbamic acid benzyl ester in 34 mL of EtOAc were hydrogenated in the presence of 0.51 g of 10% Pd/C. After removal of the catalyst and evaporation of the solvent, the residue was redissolved in 50 mL of MeOH and hydrogenated in the presence of 0.4 g of 10% Pd/C. The catalyst was removed by filtration over decalite and the filtrate was concentrated. To the residue ether and aqueous HCl were added and the layers were separated. The inorganic one was washed with ether, 1M NaOH was added and the compound was extracted with CH2Cl2, and mixtures of CH2Cl2/THF (1:1). The combined organic layers were washed with brine and dried over Na2SO4. Evaporation of the solvent yielded 2.7 g (75%) of trans-N-(2-dimethylamino-ethyl)-N-methyl-2-(4-methylamino-cyclohexyloxy)-acetamide as colorless oil, MS: 272 (MH+).

Workup

  1. customAfter removal of the catalyst and evaporation of the solvent
  2. dissolutionthe residue was redissolved in 50 mL of MeOH and hydrogenated in the presence of 0.4 g of 10% Pd/C
  3. customThe catalyst was removed by filtration over decalite
  4. concentrationthe filtrate was concentrated
  5. additionTo the residue ether and aqueous HCl were added
  6. customthe layers were separated
  7. washThe inorganic one was washed with ether, 1M NaOH
  8. additionwas added
  9. extractionthe compound was extracted with CH2Cl2, and mixtures of CH2Cl2/THF (1:1)
  10. washThe combined organic layers were washed with brine
  11. dry with materialdried over Na2SO4
  12. customEvaporation of the solvent

Sources & evidence

ORD record
ord-99eb18dbf4fb4acbb370169979360a97
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

Loading…