HCID 20148433, compound → HCID 13315116, compound

HRID 569027Notes

Reaction equation

HRID 569027 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15]2[CH:14]=[N:13][C:12](C(O)=O)=[C:11]([CH3:23])[C:10]3=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>N1C2C(=CC=CC=2)C=CC=1.[Cu]>[N:1]1([C:7]2[CH:8]=[C:9]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15]2[CH:14]=[N:13][CH:12]=[C:11]([CH3:23])[C:10]3=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 20148433HCID 20148433, compound

Product 1

HCID 13315116HCID 13315116, compoundYield 32.2%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 7047QuinolineSolvent

Procedure

2.5 g of 6-piperidino-4-methyl-β-carboline-3-carboxylic acid are heated with 520 mg of copper powder in 50 ml of quinoline for 1.5 hours to 190°-220° C. bath temperature. After distilling off the quinoline in a bulb tube, it is dispersed in ethyl acetate/10% aqueous ammonia. The precipitate that is formed is filtered off and absorptively precipated with ethanol. The combined evaporation residue of the ethanol extraction and the ethyl acetate phase yields 690 mg of 6-piperidino-4-methyl-β-carboline with a 235°-238° C. (decomposition) melting point by crystallization from ethylacetate/diisopropylether.

Workup

  1. distillationAfter distilling off the quinoline in a bulb tube
  2. additionit is dispersed in ethyl acetate/10% aqueous ammonia
  3. customThe precipitate that is formed
  4. filtrationis filtered off and absorptively precipated with ethanol
  5. customThe combined evaporation residue of the ethanol extraction

Sources & evidence

ORD record
ord-8a42dd8bae574832a6a9bfa66373b0b3
Source dataset
uspto-grants-1988_03
Patent number
US04731358

Reaction notes

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