Hydrochloric Acid → HCID 66925998, compound

HRID 40554Notes

Reaction equation

HRID 40554 reaction equation
[CH3:1][Si:2]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17](C(O)=O)[CH2:16][CH2:15]3)=[N:12][CH:13]=2)[CH2:4][CH2:3]1.Cl>ClCCl.O1CCOCC1>[CH3:1][Si:2]1([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17][CH2:16][CH2:15]3)=[N:12][CH:13]=2)[CH2:6][CH2:7]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67606033HCID 67606033, compound

Product 1

HCID 66925998HCID 66925998, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.43 g of tert-butyl ester of 4-[5-(4-methyl-4-phenyl-[1,4]azasilinan-1-yl)-pyridin-2-yl]-3,4-dihydro-2H-quinoxaline-1-carboxylic acid is put in 50 mL of dichloromethane and after cooling on an ice bath, 3.5 mL of a 4N solution of hydrochloric acid in dioxane is added. The reaction mixture is stirred for 16 h. After concentration, the mixture is taken up in dichloromethane, and neutralized by adding a saturated solution of sodium bicarbonate. After decanting, the aqueous phase is extracted with dichloromethane. The dichloromethane phases are combined and dried over sodium sulfate. After concentration under vacuum, 0.338 g of 1-[5-(4-methyl-4-phenyl[1,4]azasilinan-1-yl)-pyridin-2-yl]-1,2,3,4-tetrahydroquinoxaline is obtained.

Workup

  1. temperatureafter cooling on an ice bath
  2. concentrationAfter concentration
  3. additionby adding a saturated solution of sodium bicarbonate
  4. customAfter decanting
  5. extractionthe aqueous phase is extracted with dichloromethane
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentration under vacuum

Sources & evidence

ORD record
ord-eee1066be12e40cc9c23127a0f154336
Source dataset
uspto-grants-2013_09
Patent number
US08530473B2

Reaction notes

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