Hydrochloric Acid → HCID 22101549, compound

HRID 1457954Notes

Reaction equation

HRID 1457954 reaction equation
O1[C:5]2([CH2:10][CH2:9][N:8]([CH:11]3[CH:17]([OH:18])[C:16]([CH3:20])([CH3:19])[CH2:15][C:14](=[O:21])[C:13]([CH3:22])=[CH:12]3)[CH2:7][CH2:6]2)[O:4]CC1.Cl>C(O)C>[O:4]=[C:5]1[CH2:10][CH2:9][N:8]([CH:11]2[CH:17]([OH:18])[C:16]([CH3:19])([CH3:20])[CH2:15][C:14](=[O:21])[C:13]([CH3:22])=[CH:12]2)[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22101538HCID 22101538, compound

Product 1

HCID 22101549HCID 22101549, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To an ethanol solution (5 ml) containing the 4-(1,4-dioxa-8-aza-spiro[4.5]decan-8-yl)-5-hydroxy-2,6,6-trimethyl-2-cyclohepten-1-one obtained in Example 26 (1 g, 3.24 millimoles) there was added 6N hydrochloric acid (2 ml), and the mixture was stirred at 75° C. for 4 hours. The reaction solution was concentrated, water was added, and a 1N aqueous sodium hydroxide solution was used for neutralization. The aqueous solution was subjected to extraction with ethyl acetate and drying over anhydrous magnesium sulfate. The crude product obtained by concentration of the ethyl acetate solution was recrystallized from a benzene-hexane mixed solvent to obtain 0.53 g (60.9%) of 4-(4-oxopiperidino)-5-hydroxy-2,6,6-trimethyl-2-cyclohepten-1-one as colorless crystals.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionwater was added
  3. extractionThe aqueous solution was subjected to extraction with ethyl acetate
  4. dry with materialdrying over anhydrous magnesium sulfate
  5. customThe crude product obtained by concentration of the ethyl acetate solution
  6. customwas recrystallized from a benzene-hexane mixed solvent

Sources & evidence

ORD record
ord-676f1af2c45f451d9d482ef6a3b5c5d7
Source dataset
uspto-grants-1998_12
Patent number
US05849801

Reaction notes

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