Hydrochloric Acid → HCID 10727716, compound

HRID 1279335Notes

Reaction equation

HRID 1279335 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][S:14]2=[O:22])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(OCC)C>CC(O)C.O1CCOCC1>[NH:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][S:14]2=[O:22])[CH2:10][CH2:9]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 107345601'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxide

Product 1

HCID 10727716HCID 10727716, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

42.0 g (0.13 mole) of 1′-t-butoxycarbonylspiro[benzo[c]thiophene-1(3H),4′-piperidine]-2-oxide [prepared as described in step (b) above] were dissolved in 420 ml of 2-propanol, and 150 ml of a 4 N solution of hydrogen chloride in dioxane was added thereto, whilst ice-cooling. The mixture was then stirred for 4 hours. At the end of this time, 200 ml of diethyl ether were added to the mixture, and the mixture was allowed to stand for 1 hour, whilst ice-cooling. The precipitated crystals were then collected by filtration. The crystals were dissolved in 200 ml of a 5% w/v aqueous solution of sodium hydroxide. The product was extracted with methylene chloride, and the organic extract was dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure, to give 21.7 g of the title compound as a white amorphous product.

Workup

  1. temperaturewhilst ice-cooling
  2. waitto stand for 1 hour, whilst ice-
  3. temperaturecooling
  4. filtrationThe precipitated crystals were then collected by filtration
  5. dissolutionThe crystals were dissolved in 200 ml of a 5% w/v aqueous solution of sodium hydroxide
  6. extractionThe product was extracted with methylene chloride
  7. extractionthe organic extract
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. customThe solvent was then removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-8a89158786af4e81b8e16c9740ee852b
Source dataset
uspto-grants-2002_09
Patent number
US06448247B1

Reaction notes

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