Formic Acid → HCID 12703448, compound

HRID 1855730Notes

Reaction equation

HRID 1855730 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10]3=[CH:12][S:13][CH:14]=[C:9]3[N:8]=[C:7]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[C:6]=2[CH:22]=1.[CH:23]([OH:25])=[O:24].[BH4-].[Na+].[OH-:28].[NH4+].[OH2:30]>>[C:2]([OH:30])(=[O:28])/[CH:22]=[CH:6]/[C:23]([OH:25])=[O:24].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:23])[C:10]3=[CH:12][S:13][CH:14]=[C:9]3[N:8]=[C:7]([N:15]3[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]3)[C:6]=2[CH:22]=1

Participants

6

Reactant 5

HCID 284Formic AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 4311764Sodium borohydride2×HCID 12703443HCID 12703443, compound

Product 1

HCID 12703448HCID 12703448, compound

Procedure

A mixture of 1.8 g. of 7-chloro-9-(4-methyl-1-piperazinyl)-4H-thieno[3,4-b][1,4]benzodiazepine in 20 ml. of 95-97% formic acid is stirred and cooled. A 2 g. portion of sodium borohydride pellets is added over 30 minutes. The mixture is stirred for several hours with the incremental addition of more sodium borohydride until thin layer chromatography shows that no more starting material remains. The mixture is cooled, water is added and the mixture is made alkaline with ammonium hydroxide. The mixture is extracted with dichloromethane, the extracts are dried over magnesium sulfate and evaporated. The residue is dissolved in dichloromethane and filtered through magnesium silicate giving a glass. This glass is dissolved in 20 ml. of ethanol and a solution of 0.34 g. of fumaric acid in 4 ml. of ethanol is added. The solid is recrystallized from ethanol, giving the desired product, m.p. 222°-224° C. (dec.).

Workup

  1. additionA mixture of 1.8 g
  2. temperaturecooled
  3. temperatureThe mixture is cooled
  4. extractionThe mixture is extracted with dichloromethane
  5. dry with materialthe extracts are dried over magnesium sulfate
  6. customevaporated
  7. dissolutionThe residue is dissolved in dichloromethane
  8. filtrationfiltered through magnesium silicate giving a glass
  9. dissolutionThis glass is dissolved in 20 ml
  10. additionof ethanol is added
  11. customThe solid is recrystallized from ethanol

Sources & evidence

ORD record
ord-3b3cee5ee07242dc8ed6b6fea5ea6c31
Source dataset
uspto-grants-1980_08
Patent number
US04216148

Reaction notes

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