HCID 23316492, compound → HCID 23316499, compound

HRID 1903130Notes

Reaction equation

HRID 1903130 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[C:15]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:14]([N+:25]([O-])=O)=[CH:13][CH:12]=3)=[O:5])[CH3:2]>O1CCCC1.O.[Cl-].[Cl-].[Cl-].[Ti+3]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[C:15]([N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:14]([NH2:25])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 23316492HCID 23316492, compound

Product 1

HCID 23316499HCID 23316499, compoundYield 79.3%

Reagents, catalysts & solvents 3

HCID 10313229titanium(III) trichlorideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

140 mg of 5-piperidino-6-nitro-beta-carboline-3-carboxylic-acid-ethylester in 10 ml of tetrahydrofuran is mixed with the four-fold molar amount of titanium trichloride in water. After 6 minutes, the substance is neutralized, filtered and evaporated. The residue is extracted with methylene chloride, and the extracts are concentrated and recrystallized from glacial acetic acid. 102 mg of 5-piperidino-6-amino-beta-carboline-3-carboxylic-acid-ethylester with a m.p. of 188°-190° C. is obtained.

Workup

  1. filtrationfiltered
  2. customevaporated
  3. extractionThe residue is extracted with methylene chloride
  4. concentrationthe extracts are concentrated
  5. customrecrystallized from glacial acetic acid

Sources & evidence

ORD record
ord-91ae5d2dfaa5421c9143145841b338ef
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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