Sodium Acetate → HCID 13336358, compound

HRID 1788738Notes

Reaction equation

HRID 1788738 reaction equation
[CH2:1]([N:3]([CH2:22][CH:23]1[CH2:28][CH2:27][N:26](CC2C=CC=CC=2)[CH2:25][CH2:24]1)[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1)=[O:5])[CH3:2].C([O-])(=O)C.[Na+]>C(O)C.Cl.[Pd]>[CH2:1]([N:3]([CH2:22][CH:23]1[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]1)[C:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 20158370HCID 20158370, compound

Product 1

HCID 13336358HCID 13336358, compoundYield 64.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-Ethyl-N-[(1-benzylpiperidin-4-yl)-methyl]-2-phenylquinoline-4-carboxamide (9.6 g) is heated in ethanol (200 ml) until it has dissolved. After cooling, this solution is treated with a 4.5N ethanolic solution of hydrogen chloride (9.2 ml), 10% strength palladium-on-charcoal (2.9 g) as a catalyst and, finally, sodium acetate (1.7 g). The mixture is hydrogenated at 60° C., with stirring, under a hydrogen pressure equal to normal pressure (1 bar), for 5 hours. After 5 hours (at which time the amount of hydrogen absorbed is 470 ml), the catalyst is removed by filtration, the ethanol is evaporated off by distillation under reduced pressure, the residue is taken up in water (200 ml) and the mixture is brought to pH 10 by the addition of a concentrated solution of sodium hydroxide and extracted with ether (3×100 ml). The organic phase is washed with water (3×50 ml), dried over magnesium sulphate and evaporated under reduced pressure. N-ethyl-N-[(piperidin-4-yl)-methyl]-2-phenylquinoline-4-carboxamide (5 g) is isolated in this way; it is dissolved in acetone and converted to the monohydrochloride by the addition of a solution of hydrogen chloride in ether. This monohydrochloride melts at 219° C.

Workup

  1. dissolutionhas dissolved
  2. temperatureAfter cooling
  3. customis hydrogenated at 60° C.
  4. customAfter 5 hours (at which time the amount of hydrogen absorbed
  5. customis removed by filtration
  6. customthe ethanol is evaporated off by distillation under reduced pressure
  7. additionthe mixture is brought to pH 10 by the addition of a concentrated solution of sodium hydroxide
  8. extractionextracted with ether (3×100 ml)
  9. washThe organic phase is washed with water (3×50 ml)
  10. dry with materialdried over magnesium sulphate
  11. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-043d97be20af4fc09d3bc3b55d5c985c
Source dataset
uspto-grants-1987_08
Patent number
US04684652

Reaction notes

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