Acetic Acid → HCID 67560545, compound

HRID 1585977Notes

Reaction equation

HRID 1585977 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH:6]=[CH:7][C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][C:11]([CH3:22])=[N:10][N:9]=2)=[CH:4][CH:3]=1.C(O)(=O)C.[BH4-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>O>[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH:6]=[CH:7][C:8]2[C:14]3[CH:15]=[C:16]4[O:21][CH2:20][O:19][C:17]4=[CH:18][C:13]=3[CH2:12][CH:11]([CH3:22])[NH:10][N:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 54362632HCID 54362632, compound

Product 1

HCID 67560545HCID 67560545, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2.0 g (6.2 mmoles) of 1-(4-fluorostyryl)-4-methyl-7,8-methylenedioxy-5H-2,3-benzodiazepine prepared according to Example 86 and 10 ml of glacial acetic acid a solution of 3.0 g (79 mmoles) of sodium borohydride in 10 ml of water is added in small portions, while the temperature of the reaction mixture is kept below 35° C. The mixture is then stirred for further 2 hours and made alkaline by adding some sodium carbonate solution to it. The alkaline solution is extracted three times with 20 ml of ethyl acetate. The ethyl acetate phases are dried, evaporated and the evaporation residue is crystallized from ethanol. The crude product is purified by recrystallization from ethanol. Thus 1.39 g (69%) of substance pure on TLC is obtained. M.p.: 170-174° C.

Workup

  1. customprepared
  2. additionis added in small portions, while the temperature of the reaction mixture
  3. customis kept below 35° C
  4. extractionThe alkaline solution is extracted three times with 20 ml of ethyl acetate
  5. dry with materialThe ethyl acetate phases are dried
  6. customevaporated
  7. customthe evaporation residue is crystallized from ethanol
  8. customThe crude product is purified by recrystallization from ethanol
  9. customThus 1.39 g (69%) of substance pure on TLC is obtained

Sources & evidence

ORD record
ord-3035f0ceebef4c3bbd601c7aaaf740de
Source dataset
uspto-grants-1999_08
Patent number
US05942506

Reaction notes

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