Sodium hydride → 5,10-Dihydro-5-(3-dimethylaminopropyl)-10-methyl-6H-pyrido[3,2-b]thieno[3,4-e] [1,4]diazepin-6-one

HRID 1606459Notes

Reaction equation

HRID 1606459 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH2:6][CH2:7][CH2:8]Cl)[CH3:5].[CH3:10][N:11]1[C:17]2=[CH:18][S:19][CH:20]=[C:16]2[C:15](=[O:21])[NH:14][C:13]2[CH:22]=[CH:23][CH:24]=[N:25][C:12]1=2.Cl([O-])(=O)(=O)=O>O.CN(C)C=O>[CH3:3][N:4]([CH3:5])[CH2:6][CH2:7][CH2:8][N:14]1[C:15](=[O:21])[C:16]2=[CH:20][S:19][CH:18]=[C:17]2[N:11]([CH3:10])[C:12]2[N:25]=[CH:24][CH:23]=[CH:22][C:13]1=2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 123351PerchlorateHCID 127620225,10-dihydro-10-methyl-6H-pyrido[3,2-b]thieno[3,4-e][1,4]diazepin-6-one

Product 1

HCID 214552525,10-Dihydro-5-(3-dimethylaminopropyl)-10-methyl-6H-pyrido[3,2-b]thieno[3,4-e] [1,4]diazepin-6-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.69 g. of 55% sodium hydride-mineral oil dispersion and 0.9 ml. of dimethylaminopropylchloride in 30 ml. of dry dimethylformamide is stirred at room temperature for 0.5 hours. To the mixture is added 0.70 g. of 5,10-dihydro-10-methyl-6H-pyrido[3,2-b]thieno[3,4-e] [1,4]diazepin-6-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 amber oil, which is purified by preparative thin layer chromatography (tlc) on silica gel with 10:1 benzene:methanol as eluent to give a semi-solid. The perchlorate salt is preparaed by standard procedures and is recyrstallized from water to give a white solid, m.p. 263°-265°C. (dec.).

Workup

  1. additionA mixture of 0.69 g
  2. additionTo the mixture is added 0.70 g
  3. temperatureThe reaction mixture is cooled
  4. customquenched with water
  5. extractionextracted with chloroform
  6. concentrationThe dried chloroform extracts are concentrated to an amber oil, which
  7. customis purified by preparative thin layer chromatography (tlc) on silica gel with 10:1 benzene
  8. custommethanol as eluent to give a semi-solid
  9. customto give a white solid, m.p. 263°-265°C. (dec.)

Sources & evidence

ORD record
ord-ad4e675c8acc466ebd00d3ab95809017
Source dataset
uspto-grants-1976_04
Patent number
US03953430

Reaction notes

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