Hydrochloric Acid → HCID 13020485, compound

HRID 2198519Notes

Reaction equation

HRID 2198519 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:11]([CH2:15][C:16]([O:18]CC)=O)[NH:12][CH2:13][CH2:14][C:5]2=1.C1CCCCC1.[CH3:27][N:28]=[C:29]=[O:30].Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]1[CH:11]3[CH2:15][C:16](=[O:18])[N:28]([CH3:27])[C:29](=[O:30])[N:12]3[CH2:13][CH2:14][C:5]2=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8078CyclohexaneHCID 12228Methyl IsocyanateHCID 12876317HCID 12876317, compound

Product 1

HCID 13020485HCID 13020485, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

10 g of ethyl 6-chloro-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-1-acetate (prepared according to the patent entitled Pyridoindoles, filed by the Applicant Company on this same day) are placed in a round-bottomed flask and 150 ml of cyclohexane and 2.5 ml (1.9 g) of methyl isocyanate are added. The mixture is heated at the reflux temperature for 1 hour. It is cooled in an ice bath and filtered. This yields a white solid which is taken up in 150 ml of ethanol. The mixture is stirred and ethanol saturated with hydrogen chloride (30 ml) is added. The mixture is heated under reflux for 1 hour. It is allowed to cool and filtered. The solid is recrystallised from ethanol.

Workup

  1. waitfiled by the Applicant Company on this same day
  2. custom) are placed in a round-bottomed flask
  3. temperatureThe mixture is heated at the reflux temperature for 1 hour
  4. temperatureIt is cooled in an ice bath
  5. filtrationfiltered
  6. customThis yields a white solid which
  7. temperatureThe mixture is heated
  8. temperatureunder reflux for 1 hour
  9. temperatureto cool
  10. filtrationfiltered
  11. customThe solid is recrystallised from ethanol

Sources & evidence

ORD record
ord-c602a6cc19fd4dd9874588b58bf7972e
Source dataset
uspto-grants-1982_11
Patent number
US04358451

Reaction notes

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