Dimethylamine, hydrochloride → HCID 19825004, compound

HRID 727793Notes

Reaction equation

HRID 727793 reaction equation
O=[C:2]([CH3:26])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:16](=[O:17])[CH2:15][CH:14]3[CH2:18][S:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:13]3=[N:12]2)=[CH:7][CH:6]=1.Cl.[CH3:28][NH:29][CH3:30].C(B)#N.[Na]>C(O)C>[CH3:28][N:29]([CH3:30])[CH:2]([CH3:26])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:16](=[O:17])[CH2:15][CH:14]3[CH2:18][S:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[C:13]3=[N:12]2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 19824969HCID 19824969, compoundHCID 101953985CID 101953985

Product 1

HCID 19825004HCID 19825004, compoundYield 87.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of 3.6 g of 2-[4-(2-oxopropoxy)phenyl]-2,3,4,4a-tetrahydro-5H-(1)benzothiopyrano[4,3-c]pyridazin-3-one, 3.3 g of dimethylamine hydrochloride and 50 ml of ethanol is added dropwise 20 ml of a solution of 1 g of sodium cyanoboron hydride in 20 ml of ethanol while stirring under heating and reflux over 1 hour. The mixture is stirred under heating and reflux for further 4 hours. After the completion of the reaction, the solvent is distilled off, and water and dilute hydrochloric acid are added to the residue. After the mixture is left standing still for 30 minutes, it is neutralized with potassium carbonate and extracted with chloroform. The extract is dried over magnesium sulfate, and the solvent is distilled off. The residue is purified by silica gel column chromatography (chloroform:methanol =10:1 ) and then converted into the fumarate in acetone, which is recrystallized from ethanol to give 3.4 g of 2-[4-(2-dimethylaminopropoxy)phenyl]-2,3,4,4a-tetrahydro-5H-(1)benzothiopyrano[4,3-c]pyridazin-3-one.fumarate as white crystals, m.p. 171°-173° C.

Workup

  1. temperatureunder heating
  2. temperaturereflux over 1 hour
  3. stirringThe mixture is stirred
  4. temperatureunder heating
  5. temperaturereflux for further 4 hours
  6. customAfter the completion of the reaction
  7. distillationthe solvent is distilled off
  8. additionwater and dilute hydrochloric acid are added to the residue
  9. waitAfter the mixture is left
  10. extractionextracted with chloroform
  11. dry with materialThe extract is dried over magnesium sulfate
  12. distillationthe solvent is distilled off
  13. customThe residue is purified by silica gel column chromatography (chloroform:methanol =10:1 )
  14. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-75422097ee61456b80236d72903a56e7
Source dataset
uspto-grants-1991_09
Patent number
US05045541

Reaction notes

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