Acetic Acid → HCID 12440687, compound

HRID 1112584Notes

Reaction equation

HRID 1112584 reaction equation
CS[C:3]1[CH2:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(O)(=O)C>C(Cl)(Cl)Cl>[CH3:20][N:21]1[CH2:26][CH2:25][N:24]([C:3]2[CH2:4][C:5]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:6][C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[N:9]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 531671-MethylpiperazineHCID 371096NSC645043

Product 1

HCID 12440687HCID 12440687, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 13.3 parts of 2-methylthio-4-phenyl-3H-1,5-benzodiazepine, 26 parts by volume of 1-methylpiperazine and 1.5 part of glacial acetic acid in 150 parts by volume of chloroform is stirred at reflux temperature overnight. The solvent is then removed under reduced pressure and the residue partititoned between water and benzene. The benzene portion is washed with water and then extracted with 10% acetic acid. The acidic extract is washed with benzene and then made alkaline with concentrated ammonia. The alkaline mixture is extracted with benzene, the benzene extract washed with water and then dried over anhydrous magnesium sulfate. After the solvent is removed a crude yellow solid is obtained. The crude solid is recrystallized from a mixture of chloroform and n-hexane to yield 4-(4-methyl-1-piperazinyl)-2-phenyl-3H-1,5-benzodiazepine, melting at about 155°-157° C. This compound has the following formula ##STR16##

Workup

  1. temperatureat reflux temperature overnight
  2. customThe solvent is then removed under reduced pressure
  3. washThe benzene portion is washed with water
  4. extractionextracted with 10% acetic acid
  5. extractionThe acidic extract
  6. washis washed with benzene
  7. extractionThe alkaline mixture is extracted with benzene
  8. extractionthe benzene extract
  9. washwashed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customAfter the solvent is removed a crude yellow solid
  12. customis obtained
  13. customThe crude solid is recrystallized from a mixture of chloroform and n-hexane

Sources & evidence

ORD record
ord-fabdda5157a7452fb98c42fd65286864
Source dataset
uspto-grants-1978_10
Patent number
US04123430

Reaction notes

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