Sodium Bicarbonate → HCID 15380923, compound

HRID 610773Notes

Reaction equation

HRID 610773 reaction equation
[CH:1]1([NH:7][C:8](=[O:32])[CH2:9][CH2:10][CH2:11][CH2:12][N:13](CC2C=CC=CC=2)[CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)([O-])O.[Na+]>C(O)(=O)C.ClCCl.[Pd]>[CH:1]1([NH:7][C:8](=[O:32])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 15380922HCID 15380922, compound

Product 1

HCID 15380923HCID 15380923, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A catalyst composed of palladium on 10% moist carbon (1.5 g) is added to a solution of N-cyclohexyl-5-[benzyl{2-(2-methoxyphenoxy)ethyl}amino]pentan-amide (3 g, 6.8 mmole) in glacial acetic acid (30 ml) and the mixture is hydrogenated for 2 hours at 20° C. The catalyst is removed by filtration and the solvent is evaporated under reduced pressure. The residue obtained in the form of a salt of acetic acid is taken up in dichloromethane (50 ml) and the base is liberated by treatment with a saturated solution of sodium hydrogen carbonate. The organic phase is collected, washed with water, dried over magnesium sulfate and the solvent is evaporated under reduced pressure. The expected product is obtained in the form of a white powder after crystallisation in diethylether (0.95 g, 40%).

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvent is evaporated under reduced pressure
  3. customThe residue obtained in the form of a salt of acetic acid
  4. customThe organic phase is collected
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-29b105d75a934ead962d7185fd212f04
Source dataset
uspto-grants-1999_12
Patent number
US05998666

Reaction notes

Loading…