Water → HCID 13371578, compound

HRID 745771Notes

Reaction equation

HRID 745771 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[C:18]=1[CH3:19])=[CH:15][C:14]([C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=O)=[CH:13][CH:12]=3)=[O:5])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1.O>C1(C)C=CC=CC=1>[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[C:18]=1[CH3:19])=[CH:15][C:14]([C:20]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)=[S:37])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 13371559HCID 13371559, compound

Product 1

HCID 13371578HCID 13371578, compoundYield 127.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

400 mg of 6-piperidinocarbonyl-4-methyl-β-carboline-3-carboxylic acid ethyl ester is heated in 16 ml of toluene with 200 mg of Lawesson's reagent [2,4-bis(4-methoxyphenyl)-1,3-dithiaphosphetane-2,4-disulfide] for one hour to 100° C. Thereafter the mixture is combined with water and extracted twice with ethyl acetate. The ethyl acetate phase is dried, filtered, concentrated, and chromatographed over silica gel with methylene chloride/ethanol=10:1. Recrystallization of the corresponding fractions from ethanol/water yields 240 mg of 6-piperidinothiocarbonyl-4-methyl-β-carboline-3-carboxylic acid ethyl ester, mp 225°-230° C.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe ethyl acetate phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customchromatographed over silica gel with methylene chloride/ethanol=10:1
  6. customRecrystallization of the corresponding fractions from ethanol/water

Sources & evidence

ORD record
ord-0d070676648a43359873f0e636f852b3
Source dataset
uspto-grants-1986_07
Patent number
US04600715

Reaction notes

Loading…