HCID 68501128, compound → HCID 68501429, compound

HRID 1176462Notes

Reaction equation

HRID 1176462 reaction equation
[CH3:1][O:2][C:3]1[CH:43]=[CH:42][CH:41]=[CH:40][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[O:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][CH2:34][CH2:35][C:36]([O:38]C)=[O:37])=[CH:13][CH:12]=1>O1CCOCC1.[OH-].[Na+].O>[CH3:1][O:2][C:3]1[CH:43]=[CH:42][CH:41]=[CH:40][C:4]=1[CH2:5][O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH:18]2[O:23][CH2:24][CH2:25][O:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH2:33][CH2:34][CH2:35][C:36]([OH:38])=[O:37])=[CH:15][CH:16]=1

Participants

5

Reactant 1

HCID 68501128HCID 68501128, compound

Product 1

HCID 68501429HCID 68501429, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.30 g of methyl 4-{2-[2-(4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxy)ethoxy]phenyl}butyrate (Example 137) in 5 ml of dioxane and 2 ml of 2N NaOH is stirred at 80° C. over 7 hours. The reaction mixture is cooled to room temperature, diluted with water and washed with tert-butyl methyl ether. The combined organic phases are acidified to pH 6 with 1N HCl and subsequently extracted with ethyl acetate (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.08 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=4.37.

Workup

  1. washwashed with tert-butyl methyl ether
  2. extractionsubsequently extracted with ethyl acetate (2×)
  3. washThe combined organic phases are washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0949e0e5c6054b26b6e9e23486c8f302
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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