Hydrochloric Acid → HCID 66863860, compound

HRID 1510054Notes

Reaction equation

HRID 1510054 reaction equation
C(OC([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[N:23]=[CH:22][C:21]([CH:24]3[CH2:29][CH2:28][N:27]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH2:26][CH2:25]3)=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>ClCCl>[C:30]([N:27]1[CH2:28][CH2:29][CH:24]([C:21]2[CH:22]=[N:23][C:18]([N:11]3[C:12]4[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=4)[NH:8][CH2:9][CH2:10]3)=[CH:19][CH:20]=2)[CH2:25][CH2:26]1)([CH3:33])([CH3:31])[CH3:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66863357HCID 66863357, compound

Product 1

HCID 66863860HCID 66863860, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(1′-(tert-Butyl)-1′,2′,3′,4′,5′,6′-hexahydro-3,4′-bipyridinyl-6-yl)-3,4-dihydro-2H-quinoxaline-1-carboxylic acid tert-butyl ester (0.166 g, 0.37 mmol) is placed in 0.65 ml of dichloromethane at 0° C. and then 4N HCl in dioxane (1.4 ml, 5.59 mmol) is added. The reaction medium is stirred at ambient temperature for 18 h. After concentrating to dryness, the reaction medium is hydrolysed with 20 ml of H2O and then K2CO3 is added until a pH of 10 is reached. The aqueous phase is extracted with ethyl acetate. The organic phase is then washed with a saturated aqueous sodium chloride solution, then dried over MgSO4 and concentrated to dryness. 0.12 g of 1-(1′-(tert-butyl)-1′,2′,3′,4′,5′,6′-hexahydro-3,4′-bipyridinyl-6-yl)-1,2,3,4-tetrahydroquinoxaline is obtained.

Workup

  1. concentrationAfter concentrating to dryness
  2. additionK2CO3 is added until a pH of 10
  3. extractionThe aqueous phase is extracted with ethyl acetate
  4. washThe organic phase is then washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bcc1aa0dfc734cc3a64d92ecd535ab5e
Source dataset
uspto-grants-2012_07
Patent number
US08211892B2

Reaction notes

Loading…