Sodium Hydroxide → HCID 10076286, compound

HRID 1782777Notes

Reaction equation

HRID 1782777 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][O:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:38]=[CH:37][C:36]([C:39]([O:41]C)=[O:40])=[CH:35][C:22]=3[C:23]([N:25]3[CH2:30][CH2:29][CH:28]([C:31]([O:33]C)=[O:32])[CH2:27][CH2:26]3)=[O:24])=[CH:13][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[C:39]([C:36]1[CH:37]=[CH:38][C:21]([O:20][CH2:19][CH2:18][CH2:17][C:14]2[CH:13]=[CH:12][C:11]([O:10][CH2:9][CH2:8][CH2:7][CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[CH:16][CH:15]=2)=[C:22]([CH:35]=1)[C:23]([N:25]1[CH2:26][CH2:27][CH:28]([C:31]([OH:33])=[O:32])[CH2:29][CH2:30]1)=[O:24])([OH:41])=[O:40]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57589071HCID 57589071, compound

Product 1

HCID 10076286HCID 10076286, compoundYield 87.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Absolution of 10.4 g of methyl 1-[2-{3-[4-(3-cyclohexylpropoxy)phenyl]propoxy}-5-(methoxycarbonyl)benzoyl]piperidine-4-carboxylate in a mixture of 160 ml of THF and 160 ml of methanol is mixed with 160 ml of 2 molar sodium hydroxide solution and stirred at a temperature of 60° C. for 1 hour. The organic solvents are then removed as far as possible in a rotary evaporator. 165 ml of 2 molar hydrochloric acid are added to the remaining aqueous solution with stirring. A precipitate separates out. Precipitation is completed by stirring at 0° C. The precipitate is filtered off with suction and washed with water. The crude product is purified by recrystallization from a solvent mixture composed of 250 ml of acetone and 200 ml of water. 8.7 g of a solid are obtained and are again heated to reflux in a mixture of 300 ml of water and 100 ml of acetone for 6 hours. Cooling to 0° C., filtration, washing with water and drying result in 8.6 g of a solid.

Workup

  1. customThe organic solvents are then removed as far as
  2. custompossible in a rotary evaporator
  3. addition165 ml of 2 molar hydrochloric acid are added to the remaining aqueous solution
  4. stirringwith stirring
  5. customPrecipitation
  6. stirringby stirring at 0° C
  7. filtrationThe precipitate is filtered off with suction
  8. washwashed with water
  9. customThe crude product is purified by recrystallization from a solvent mixture

Sources & evidence

ORD record
ord-2aa9e34625c8478d9224be26a4d12629
Source dataset
uspto-grants-2009_03
Patent number
US07498460B2

Reaction notes

Loading…