Hydrochloric Acid → HCID 68505124, compound

HRID 1176291Notes

Reaction equation

HRID 1176291 reaction equation
[CH3:1][O:2][C:3]1[CH:42]=[CH:41][CH:40]=[CH:39][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][C:35]([O:37]C)=[O:36])=[CH:13][CH:12]=1.Cl>O1CCOCC1.[OH-].[Na+]>[CH3:1][O:2][C:3]1[CH:42]=[CH:41][CH:40]=[CH:39][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][C:35]([OH:37])=[O:36])=[CH:15][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68500953HCID 68500953, compound

Product 1

HCID 68505124HCID 68505124, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 0.057 g of methyl 3-{2-[2-(4-{4-[3-(2-Methoxybenzyloxy)propoxy]phenyl}piperidin-3-yloxy)ethoxy]phenyl}propionate (Example 52) in 1 ml of dioxane and 0.2 ml of 2N NaOH is stirred at 80° C. over 40 minutes. The reaction mixture is cooled to room temperature and made neutral with 0.5N HCl. The mixture is subsequently extracted with ethyl acetate (3×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The crude title compound is obtained as a yellow solid from the residue. Rt=4.26.

Workup

  1. temperatureThe reaction mixture is cooled to room temperature
  2. extractionThe mixture is subsequently extracted with ethyl acetate (3×)
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f419385a9fc346f488931882c5f8ffb4
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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