Hydrochloric Acid → HCID 10727716, compound

HRID 278947Notes

Reaction equation

HRID 278947 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

In 420 ml of 2-propanol, 42.0 g (0.13 mole) of the 1′-tert-butoxycarbonyl-spiro[benzo[c]thiophene-1(3H),4′-piperidin]-2-oxide obtained in Referential Example 1(b) were dissolved, followed by addition of 150 ml of a 4N solution of hydrogen chloride in dioxan under ice-cooling, and the mixture was stirred for 4 hours. To the reaction mixture, 200 ml of diethyl ether were added. After, the mixture was allowed to stand for 1 hour under ice-cooling, to afford crystals. The crystals were collected by filtration. The resulting crystals were dissolved in 200 ml of a 5% aqueous solution of sodium hydroxide. The solution was extracted with methylene chloride. The organic layer was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure, whereby 21.7 g of the title compound was obtained as a white amorphous product.

Workup

  1. dissolutionwere dissolved
  2. temperaturecooling
  3. waitto stand for 1 hour under ice-
  4. temperaturecooling
  5. customto afford crystals
  6. filtrationThe crystals were collected by filtration
  7. dissolutionThe resulting crystals were dissolved in 200 ml of a 5% aqueous solution of sodium hydroxide
  8. extractionThe solution was extracted with methylene chloride
  9. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  10. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d328c1d033e648829084e32a7de45808
Source dataset
uspto-grants-2002_03
Patent number
US06362179B1

Reaction notes

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