Sodium hydride → HCID 21329384, compound

HRID 614388Notes

Reaction equation

HRID 614388 reaction equation
[H-].[Na+].[CH2:3]1[C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[NH:10][C:9]=2[CH2:8][CH2:7][CH2:6][S:5](=[O:19])(=[O:18])[CH2:4]1.[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24]Cl>CN(C)C=O>[CH3:20][N:21]([CH3:26])[CH2:22][CH2:23][CH2:24][N:10]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:16]=2[C:17]2[CH2:3][CH2:4][S:5](=[O:18])(=[O:19])[CH2:6][CH2:7][CH2:8][C:9]1=2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 21329386HCID 21329386, compound

Product 1

HCID 21329384HCID 21329384, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
90 °C

Procedure

To a suspension of 2.1g (0.05 mole) of sodium hydride (57% dispersion in mineral oil) in 25 ml of dimethylformamide is added a solution of 12.47g (0.05 mole) of 1,2,4,5,6,7-hexahydrothiocino[5,4-b]indole 3,3-dioxide in 50 ml of dimethylformamide with stirring under nitrogen. The resulting mixture is stirred at 30°-35° C. for one hour. A solution of 6.03g (0.05 mole) of 3-dimethylaminopropyl chloride (freshly distilled) in 25 ml of dimethylformamide is added and the mixture is stirred at room temperature for one hour and then heated in a wax bath at 90° C. for five hours. The dimethylformamide is removed in vacuo. The residue is dissolved in 10% hydrochloric acid and extracted with ether. The aqueous layer is made basic with sodium hydroxide and extracted with ether. The ether layer is washed with water, dried over sodium sulfate and the solvent is removed. Recrystallization from isopropyl ether gives 10.7g (64%) of an analytical sample, m.p. 119°-120° C.

Workup

  1. stirringThe resulting mixture is stirred at 30°-35° C. for one hour
  2. additionis added
  3. stirringthe mixture is stirred at room temperature for one hour
  4. customThe dimethylformamide is removed in vacuo
  5. dissolutionThe residue is dissolved in 10% hydrochloric acid
  6. extractionextracted with ether
  7. extractionextracted with ether
  8. washThe ether layer is washed with water
  9. dry with materialdried over sodium sulfate
  10. customthe solvent is removed
  11. customRecrystallization from isopropyl ether
  12. customgives 10.7g (64%) of an analytical sample, m.p. 119°-120° C.

Sources & evidence

ORD record
ord-15780702b13b402d971dc63dc7d09ac5
Source dataset
uspto-grants-1979_03
Patent number
US04144349

Reaction notes

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