Hydrochloric Acid → HCID 67778318, compound

HRID 1756000Notes

Reaction equation

HRID 1756000 reaction equation
C([N:9]1[CH2:14][CH2:13][C:12]2([CH2:23][C:22]3[C:17](=[CH:18][C:19]([O:24][CH3:25])=[CH:20][CH:21]=3)[C:16](=[O:26])[CH2:15]2)[CH2:11][CH2:10]1)(=O)C1C=CC=CC=1.[ClH:27]>C(O)C.O>[ClH:27].[CH3:25][O:24][C:19]1[CH:18]=[C:17]2[C:22]([CH2:23][C:12]3([CH2:15][C:16]2=[O:26])[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]3)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67783580HCID 67783580, compound

Product 1

HCID 67778318HCID 67778318, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A solution of N-Benzoyl-3,4-dihydro-7-methoxyspiro-[naphthalene-3,4'-piperidine]-1-one (3.4 g, 7.8 mmole) in ethanol (100 mL) is treated with 6 N HCl (100 mL) and heated to reflux for 5 hours. The reaction is cooled to 90 ° C. and heated at this temperature for 16 hours. The reaction is cooled to room temperature, diluted with 300 mL water and extracted with two 75 mL portions of ethyl acetate. The aqueous phase is then diluted with ethanol (1 L) and concentrated at reduced pressure to dryness. The residue is crystallized from ethanol (100 mL) to give the product as the hydrochloride.

Workup

  1. temperatureheated
  2. temperatureto reflux for 5 hours
  3. temperatureheated at this temperature for 16 hours
  4. temperatureThe reaction is cooled to room temperature
  5. extractionextracted with two 75 mL portions of ethyl acetate
  6. additionThe aqueous phase is then diluted with ethanol (1 L)
  7. concentrationconcentrated at reduced pressure to dryness
  8. customThe residue is crystallized from ethanol (100 mL)

Sources & evidence

ORD record
ord-3435067de277464388bc2f91d94e979e
Source dataset
uspto-grants-1995_08
Patent number
US05439914

Reaction notes

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