Sodium hydride → 4,9-Dihydro-9-(3-dimethylaminopropyl)-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

HRID 436133Notes

Reaction equation

HRID 436133 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7](=[O:15])[C:6]2=[CH:16][S:17][CH:18]=[C:5]12.[CH3:19][N:20]([CH2:22][CH2:23][CH2:24]Cl)[CH3:21]>CN(C)C=O>[CH3:19][N:20]([CH3:21])[CH2:22][CH2:23][CH2:24][N:8]1[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N:4]([CH3:3])[C:5]2=[CH:18][S:17][CH:16]=[C:6]2[C:7]1=[O:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 125216424,9-Dihydro-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Product 1

HCID 214552344,9-Dihydro-9-(3-dimethylaminopropyl)-4-methyl-10H-thieno[3,4-b][1,5]benzodiazepin-10-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.3 g. of 55% sodium hydride-mineral oil dispersion and 0.35 g. of 4,9-dihydro-4-methyl-10H-thieno-[3,4-b][1,5]benzodiazepin-10-one in 25 ml. of dry dimethylformamide is stirred at room temperature for 0.5 hours. To the mixture is added 0.45 g. of dimethylaminopropyl chloride and stirring at room temperature is continued for 18 hours. The reaction mixture is cooled, quenched with water, acidified, decolorized and filtered. The filtrate is made alkaline and extracted with chloroform. The dried chloroform extracts are concentrated under reduced pressure to give an oil which is crystallized by dissolving in boiling hexane and a minimal volume of ethyl acetate and cooling to give off-white crystals, m.p. 52°-56° C.

Workup

  1. additionA mixture of 0.3 g
  2. additionTo the mixture is added 0.45 g
  3. temperatureThe reaction mixture is cooled
  4. customquenched with water
  5. filtrationfiltered
  6. extractionextracted with chloroform
  7. concentrationThe dried chloroform extracts are concentrated under reduced pressure
  8. customto give an oil which
  9. customis crystallized
  10. dissolutionby dissolving
  11. temperaturea minimal volume of ethyl acetate and cooling
  12. customto give off-white crystals, m.p. 52°-56° C.

Sources & evidence

ORD record
ord-303f42ecf635484681fd45d15d6b92dc
Source dataset
uspto-grants-1977_02
Patent number
US04007272

Reaction notes

Loading…