Hydrochloric Acid → HCID 66835954, compound

HRID 2404456Notes

Reaction equation

HRID 2404456 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:26][CH:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1)[C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][O:22]C(=O)C)[CH:14]=[CH:15][CH:16]=1.O1CCOCC1.[OH-].[Na+].Cl>O.CO>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH:10]([O:26][CH:27]1[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]1)[C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH2:19][CH2:20][CH2:21][OH:22])[CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 66836043HCID 66836043, compound

Product 1

HCID 66835954HCID 66835954, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of Acetic acid 5-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}pent-4-enyl ester (150 mg) in a mixture of water (1 mL), 1,4-dioxane (1 mL) and methanol (1 mL) is added 1N sodium hydroxide solution (0.6 mL). The reaction mixture is stirred at room temperature for 2 hours. After neutralization to pH 7 with addition of 1N hydrochloric acid, the reaction mixture is extracted with dichloromethane. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 95/5/0.5 to 90/10/1) to afford 5-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenyl}pent-4-en-1-ol.

Workup

  1. extractionthe reaction mixture is extracted with dichloromethane
  2. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 95/5/0.5 to 90/10/1)

Sources & evidence

ORD record
ord-f026998a4324429794f57fcae1b69488
Source dataset
uspto-grants-2014_08
Patent number
US08802664B2

Reaction notes

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