Water → HCID 68120221, compound

HRID 2397577Notes

Reaction equation

HRID 2397577 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]3[CH2:11][CH2:12][NH:13][C:14](=[O:15])[C:6]3=[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]=2[CH:3]=1.[H-].[Na+].[CH3:24][N:25]([CH2:27][CH2:28]CCl)[CH3:26].O.[CH3:32]N(C=O)C>>[CH3:24][N:25]([CH3:26])[CH:27]([CH3:28])[CH2:32][N:13]1[CH2:12][CH2:11][N:7]2[C:8]3[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=3[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:6]2[C:14]1=[O:15]

Participants

6

Reactant 5

HCID 962WaterHCID 6228Dimethylformamide3×HCID 24758Sodium hydrideHCID 669603-Chloro-N,N-dimethyl-1-propanamineHCID 21436045HCID 21436045, compound

Product 1

HCID 68120221HCID 68120221, compound

Conditions

Temperature
50 °C

Procedure

A solution of 4.5 grams (0.015 mole) 8-chloro-10-phenyl-1,2,3,4-tetrahydropyrazino[1,2-a]indole-1-one in 30 ml DMF, is added to a suspension of sodium hydride (1 gram of 50% dispersion, 0.02 mole) in 20 ml DMF. After stirring at 34°-40° C. for 20 minutes a solution of freshly distilled dimethylaminopropyl chloride (1.8 grams, 0.015 moles) in 5 ml DMF is added dropwise. Stirring is continued and the reaction mixture is heated at 50° C. for 8 hours. The mixture is cooled, and poured into cold water (300 ml). This is extracted 5 times with methylenedichloride. The extracts are washed well with saline. After drying the extract over sodium sulfate, the drying agent is filtered off and the filtrate is concentrated. The residue is diluted with ether. The product crystallizes out and is filtered off. Recrystallization from heptane gives 3.4 grams (62%) of above titled product, m.p. 151°-52° C.

Workup

  1. additionis added dropwise
  2. temperatureThe mixture is cooled
  3. extractionThis is extracted 5 times with methylenedichloride
  4. washThe extracts are washed well with saline
  5. customAfter drying the
  6. extractionextract over sodium sulfate
  7. filtrationthe drying agent is filtered off
  8. concentrationthe filtrate is concentrated
  9. additionThe residue is diluted with ether
  10. customThe product crystallizes out
  11. filtrationis filtered off
  12. customRecrystallization from heptane

Sources & evidence

ORD record
ord-07cfd0675a614e988aa5b86b710790de
Source dataset
uspto-grants-1977_05
Patent number
US04022778

Reaction notes

Loading…