Water → Depyrazine 7,8-Dinitrophenyl Varenicline

HRID 2187560Notes

Reaction equation

HRID 2187560 reaction equation
[N+:1]([C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]2[CH:11]3[CH2:18][CH:7]([CH2:8][N:9](C(=O)C(F)(F)F)[CH2:10]3)[C:6]=2[CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Na+].[Na+].O.CO.C(Cl)Cl>CO>[N+:15]([C:14]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]2[CH:7]3[CH2:18][CH:11]([CH2:10][NH:9][CH2:8]3)[C:12]=2[CH:13]=1)([O-:17])=[O:16]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 21226129Dichloromethane methanolHCID 218647441-(7,8-Dinitro-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one

Product 1

HCID 9878181Depyrazine 7,8-Dinitrophenyl Varenicline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-triflouroethanone (3.7 g, 10.7 mmol) and Na2CO3 (2.3 g, 21.4 mmol) were combined in MeOH (50 mL)) and H2O (20 mL) then warmed to reflux for 18 hours. The reaction was cooled, concentrated, treated with H2O and extracted with CH2Cl2 (3×50 mL) then dried through a cotton plug. After concentration. the residue was chromatographed to provide brown solids. (1.9 g. 71%). (TLC 5% MeOH/CH2Cl2 (NH3) Rf0.36). 1H NMR (400 MHz, CDCl3) δ7.69 (s, 2H), 3.17 (br s, 2H), 3.11 (d, J=12.6 Hz, 2H), 2.53 (m, 1H), 2.07 (d, J=11.0 Hz, 1H). GCMS m/e 249 (M+).

Workup

  1. temperaturethen warmed
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. additiontreated with H2O
  6. extractionextracted with CH2Cl2 (3×50 mL)
  7. customthen dried through a cotton plug
  8. concentrationAfter concentration
  9. customthe residue was chromatographed
  10. customto provide brown solids

Sources & evidence

ORD record
ord-c8abf7582ecb4b2ab0b8467e63cc20e6
Source dataset
uspto-grants-2002_06
Patent number
US06410550B1

Reaction notes

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