Hydrochloric Acid → HCID 12952389, compound

HRID 1284460Notes

Reaction equation

HRID 1284460 reaction equation
[ClH:1].C([O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20](=[O:30])[CH:21]([CH3:29])[CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[CH:14]=[CH:13]2)C1C=CC=CC=1.Cl.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[ClH:1].[OH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[CH:16]=[C:15]([C:20](=[O:30])[CH:21]([CH3:29])[CH2:22][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)[CH:14]=[CH:13]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 12952387HCID 12952387, compound

Product 1

HCID 12952389HCID 12952389, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3.3 g of 6'-benzyloxy-2-methyl-3-piperidino-2'-propionaphthone hydrochloride, 5 ml of concentrated hydrochloric acid and 40 ml of acetic acid was agitated under heating at 90° C. for 6 hours. Aqueous solution of sodium bicarbonate was added thereto, and the mixture was extracted with ether-ethyl acetate (2:1). After washing with water, 1% hydrochloric acid was added to move the object product to aqueous phase. It was washed with ether-ethyl acetate and made to be alkaline by aqueous solution of sodium bicarbonate, and then extracted by ether. After washing with water and drying, purification by silica gel column chromatography and active carbon treatment were conducted. Crystals obtained by concentrating under reduced pressure were recrystallized from ethanol-ether, thus producing 1.0 g of 6'-hydroxy-2-methyl-3-piperidino-2'-propionaphthone hydrochloride of light-brown crystals. m.p. 188°-189° C.

Workup

  1. extractionthe mixture was extracted with ether-ethyl acetate (2:1)
  2. washAfter washing with water, 1% hydrochloric acid
  3. additionwas added
  4. washIt was washed with ether-ethyl acetate
  5. extractionextracted by ether
  6. washAfter washing with water
  7. customdrying
  8. custompurification by silica gel column chromatography and active carbon treatment
  9. customCrystals obtained
  10. concentrationby concentrating under reduced pressure
  11. customwere recrystallized from ethanol-ether

Sources & evidence

ORD record
ord-089c7c5563ca42de87967f80b27f4b1e
Source dataset
uspto-grants-1986_01
Patent number
US04563454

Reaction notes

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