Hydrochloric Acid → 9-(2-Dimethylamino-1-methylethyl)-4,9-dihydro-4-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one, hydrochloride

HRID 436134Notes

Reaction equation

HRID 436134 reaction equation
[H-].[Na+].Cl.[CH3:4][N:5]([CH3:10])[CH2:6][CH:7]([Cl:9])[CH3:8].[CH3:11][N:12]1[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[NH:16][C:15](=[O:23])[C:14]2=[CH:24][S:25][CH:26]=[C:13]12.Cl>C(O)C.CCOCC.CN(C)C=O>[ClH:9].[CH3:4][N:5]([CH3:10])[CH2:6][CH:7]([N:16]1[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N:12]([CH3:11])[C:13]2=[CH:26][S:25][CH:24]=[C:14]2[C:15]1=[O:23])[CH3:8]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 942942-Chloropropyldimethylamine hydrochlorideHCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 1317101509-(2-Dimethylamino-1-methylethyl)-4,9-dihydro-4-methyl-10H-thieno[3,4-b] [1,5]benzodiazepin-10-one, hydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.47 g. of 55% sodium hydride-mineral oil dispersion and 0.83 g. of 2-dimethylamino-1-methylethylchloride hydrochloride in 30 ml. of dry dimethylformamide is stirred at room temperature for 0.5 hours. To the mixture is added 0.6 g. of 4,9-dihydro-4-methyl-10H-thieno[3,4-b][1,5]-benzodiazepin-10-one and stirring is continued for 18 hours. The reaction mixture is cooled, quenched with water and extracted with chloroform. The dried chloroform extracts are concentrated to an oil which is chromatographed on silica gel preparative thin layer chromatographic (tlc) plates using 10:1 benzene:methanol to give a yellow oil. The oil is dissolved in ethanol and treated with anhydrous hydrogen chloride followed by dilution with ether to give a solid, which is recrystallized from ethanol to give white crystals, m.p. 280°-282° C. (dec.).

Workup

  1. additionA mixture of 0.47 g
  2. additionTo the mixture is added 0.6 g
  3. temperatureThe reaction mixture is cooled
  4. customquenched with water
  5. extractionextracted with chloroform
  6. concentrationThe dried chloroform extracts are concentrated to an oil which
  7. customis chromatographed on silica gel preparative thin layer chromatographic (tlc) plates
  8. custommethanol to give a yellow oil
  9. customto give a solid, which
  10. customis recrystallized from ethanol
  11. customto give white crystals, m.p. 280°-282° C. (dec.)

Sources & evidence

ORD record
ord-cd441f10b5b84517b2eefd078df66efa
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

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