Hydrochloric Acid → HCID 67188496, compound

HRID 551800Notes

Reaction equation

HRID 551800 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17](C(OC(C)(C)C)=O)[CH2:16][CH2:15]3)=[O:13])[CH2:8]2)[CH:2]=1.Cl>O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[CH2:11][CH2:10][N:9]([C:12]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][CH2:16][CH2:15]3)=[O:13])[CH2:8]2)[CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67189427HCID 67189427, compound

Product 1

HCID 67188496HCID 67188496, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

3.72 g of tert-butyl 4-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-3,4-dihydroquinoxaline-1(2H)-carboxylate, dissolved in 18.2 ml of dioxane, are introduced into a 250 ml round-bottomed flask. 34.1 ml of a 4N solution of hydrochloric acid in dioxane are subsequently added. Stirring is maintained for three hours. After evaporating, the residue is taken up in dichloromethane and a saturated aqueous sodium hydrogencarbonate solution and then the aqueous phase is extracted three times with dichloromethane. The organic phases are combined and dried over sodium sulfate and the solvent is evaporated under reduced pressure. 2.6 g of 1-[(3-(pyridin-3-yl)pyrrolidin-1-yl)carbonyl]-1,2,3,4-tetrahydroquinoxaline are obtained.

Workup

  1. additionare introduced into a 250 ml round-bottomed flask
  2. temperatureis maintained for three hours
  3. customAfter evaporating
  4. extractiona saturated aqueous sodium hydrogencarbonate solution and then the aqueous phase is extracted three times with dichloromethane
  5. dry with materialdried over sodium sulfate
  6. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-25f2a68dba3145ca8bf61686f2adad97
Source dataset
uspto-grants-2011_05
Patent number
US07947834B2

Reaction notes

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