Formic Acid → HCID 12703446, compound

HRID 1855728Notes

Reaction equation

HRID 1855728 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[NH:12][C:11]3=[CH:19][S:20][CH:21]=[C:10]3[N:9]=2)[CH2:4][CH2:3]1.[CH:22]([OH:24])=[O:23].[BH4-].[Na+].[OH-:27].[NH4+].[OH2:29]>>[C:11]([OH:29])(=[O:27])/[CH:10]=[CH:21]/[C:22]([OH:24])=[O:23].[CH3:22][N:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)=[N:9][C:10]2=[CH:21][S:20][CH:19]=[C:11]12

Participants

6

Reactant 5

HCID 284Formic AcidHCID 962WaterHCID 14923Ammonium HydroxideHCID 30577014H-Thieno(3,4-b)(1,4)benzodiazepine, 9-(4-methyl-1-piperazinyl)-HCID 4311764Sodium borohydride

Product 1

HCID 12703446HCID 12703446, compound

Procedure

A solution of 1.8 g. portion of 9-(4-methyl-1-piperazinyl)-4H-thieno[3,4-b][1,4]benzodiazepine in 21 ml. of 97% formic acid is cooled in an ice bath and 2.1 g. of sodium borohydride pellets are added portionwise over a 30 minute period. The mixture is stirred for 2 hours, cooled, water is added, the mixture is made alkaline with ammonium hydroxide and extracted with chloroform. The extract is dried over magnesium sulfate, filtered and evaporated. The residue is dissolved in 15 ml. of warm ethanol, filtered and 0.7 g. of fumaric acid in 10 ml. of ethanol is added giving the desired compound as the fumarate salt, m.p. 206°-208° C. (dec.).

Workup

  1. temperaturecooled
  2. extractionextracted with chloroform
  3. dry with materialThe extract is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue is dissolved in 15 ml
  7. filtrationof warm ethanol, filtered
  8. additionof ethanol is added

Sources & evidence

ORD record
ord-8e21069b1a4e44d7bd823ef31c9d9af4
Source dataset
uspto-grants-1980_08
Patent number
US04216148

Reaction notes

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