Hydrochloric Acid → HCID 21939878, compound

HRID 1242913Notes

Reaction equation

HRID 1242913 reaction equation
Cl.C([N:5]1[CH2:10][CH2:9][CH2:8][CH:7]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:15][CH:14]=2)=[O:12])[CH2:6]1)(=O)C>>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([C:11]([CH:7]2[CH2:8][CH2:9][CH2:10][NH:5][CH2:6]2)=[O:12])=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 21939883HCID 21939883, compound

Product 1

HCID 21939878HCID 21939878, compoundYield 78.1%

Conditions

Temperature
100 °C

Procedure

Concentrated hydrochloric acid (53 ml) was added to 2-[4-[(1-acetyl-3-piperidinyl)carbonyl]phenyl]-1H-isoindol-1,3 (2H)-dione (4.00 g, 10.6 mmol) obtained in Reference Example 76, which was stirred at 100° C. for 16 hours, and then insoluble matters were filtered off. Potassium carbonate was added to the filtrate to make it alkaline, and extraction was conducted using ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and then the solvent was distilled out under reduced pressure. The resulting residue was powdered with diisopropyl ether, to give (4-aminophenyl) (3-piperidinyl)methanone (1.69 g).

Workup

  1. customobtained in Reference Example 76, which
  2. filtrationinsoluble matters were filtered off
  3. additionPotassium carbonate was added to the filtrate
  4. extractionextraction
  5. washThe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled out under reduced pressure

Sources & evidence

ORD record
ord-2fa5ca48dc1445a4a2c13ac5b973a102
Source dataset
uspto-grants-2006_10
Patent number
US07115750B1

Reaction notes

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