Hydrochloric Acid → Chlorphentermine

HRID 2172710Notes

Reaction equation

HRID 2172710 reaction equation
ClCC([NH:5][C:6]([CH3:16])([CH3:15])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=1)=O.Cl.C(=O)(O)[O-].[Na+]>O1CCOCC1>[Cl:14][C:11]1[CH:10]=[CH:9][C:8]([CH2:7][C:6]([CH3:16])([NH2:5])[CH3:15])=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68378991HCID 68378991, compound

Product 1

HCID 10007ChlorphentermineYield 38.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
105 °C

Procedure

To a mixture of 2-chloro-N-(1-(4-chlorophenyl)-2-methylpropan-2-yl)acetamide (259 mg, 1.00 mmol) in dioxane (5.0 mL) was added conc. hydrochloric acid (20 mL). After stirring at 105° C. for 16 hours, the reaction mixture was poured onto ice and basified by the addition of saturated aq. sodium bicarbonate to pH>8. The mixture was extracted with ethyl acetate and the combined organic fractions were washed with water, dried over sodium sulfate and concentrated under vacuum. The crude product was then purified by reverse phase flash chromatography (0 to 25% acetonitrile in aq. 0.01% formic acid) to give 1-(4-chlorophenyl)-2-methylpropan-2-amine (70 mg, 38% yield) as a white solid.

Workup

  1. additionthe reaction mixture was poured onto ice
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe combined organic fractions were washed with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product was then purified by reverse phase flash chromatography (0 to 25% acetonitrile in aq. 0.01% formic acid)

Sources & evidence

ORD record
ord-8decfc3e05914843a289ee7ff1afa9bb
Source dataset
uspto-grants-2015_06
Patent number
US09056852B2

Reaction notes

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