Hydrochloric Acid → HCID 86629974, compound

HRID 657636Notes

Reaction equation

HRID 657636 reaction equation
[H-].[Na+].[CH:3](OC)=[O:4].[CH3:7][C@H:8]1[CH2:13][C@H:12]([CH3:14])[CH2:11][N:10]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=2)[CH2:9]1.Cl>O1CCCC1>[CH3:14][C@H:12]1[CH2:13][C@H:8]([CH3:7])[CH2:9][N:10]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH2:26][CH:3]=[O:4])=[CH:21][CH:20]=2)[CH2:11]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7865Methyl formateHCID 24758Sodium hydrideHCID 9795992HCID 9795992, compound

Product 1

HCID 86629974HCID 86629974, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (82 mg, 60% in paraffin) are added methyl formate (150 μL) and a solution of trans-3,5-dimethyl-1-[3-(4-acetylphenoxy)propyl]piperidine (610 mg) in tetrahydrofuran (0.4 mL). The mixture is stirred for two hours at room temperature then hydrolysed with a 1N aqueous hydrochloric acid solution keeping the pH alkaline. The solution is extracted twice with ethyl acetate. The extracts are pooled, dried over magnesium sulphate, concentrated under reduced pressure and purified by chromatography over silica gel with a gradient dichloromethane/methanol from 100/0 to 95/5. Fractions containing the expected product are pooled, concentrated under reduced pressure to give 100 mg of trans-3,5-dimethyl-1-{3-[4-(3-oxopropanoyl)phenoxy]propyl}piperidine as a pale yellow oil that is used rapidly, without further purification in the next step.

Workup

  1. extractionThe solution is extracted twice with ethyl acetate
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated under reduced pressure
  4. custompurified by chromatography over silica gel with a gradient dichloromethane/methanol from 100/0 to 95/5
  5. additionFractions containing the expected product
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9b3feb5de2e74c9eaf06f8718d527bd3
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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