Sodium Hydroxide → 10,11-Dihydro-5-methyl-dibenzo[b,e][1,4]diazepine

HRID 1826673Notes

Reaction equation

HRID 1826673 reaction equation
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][N:5](C(=O)C(F)(F)F)[C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]1=2.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][NH:5][C:4]2[CH:19]=[CH:20][CH:21]=[CH:22][C:3]1=2

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 221352361-(10,11-Dihydro-5-methyl-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone

Product 1

HCID 2213523710,11-Dihydro-5-methyl-dibenzo[b,e][1,4]diazepineYield 94.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(10,11-Dihydro-5-methyl-dibenzo[b,e][1,4]diazepin-10-yl)-2,2,2-trifluoroethanone of Step B (1.0 g) in ethanol (25 mL) was treated with 1 N sodium hydroxide (10 mL). The reaction mixture was refluxed for five hours, cooled, all volatiles removed in vacuo and the residue triturated with water. The resulting solid was filtered off, redissolved in dichloromethane and dried over anhydrous sodium sulfate. The solution was filtered through a short column of Magnesol® which was eluted with several additional volumes of dichloromethane. The total effluent was evaporated to dryness to provide the title compound as an off-white crystalline solid (0.65 g), m.p. 115–117° C.

Workup

  1. temperatureThe reaction mixture was refluxed for five hours
  2. temperaturecooled
  3. customall volatiles removed in vacuo
  4. customthe residue triturated with water
  5. filtrationThe resulting solid was filtered off
  6. dissolutionredissolved in dichloromethane
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationThe solution was filtered through a short column of Magnesol® which
  9. washwas eluted with several additional volumes of dichloromethane
  10. customThe total effluent was evaporated to dryness

Sources & evidence

ORD record
ord-53090b7ec909428da75a92864c57404e
Source dataset
uspto-grants-2006_05
Patent number
US07053083B2

Reaction notes

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