Water → HCID 13136251, compound

HRID 1903119Notes

Reaction equation

HRID 1903119 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)=[CH:15][C:14]([C:19]#[C:20][CH2:21]Cl)=[CH:13][CH:12]=3)=[O:5])[CH3:2].[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.N12CCCCC1C=NCCC2.O>C(O)C>[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)=[CH:15][C:14]([C:19]#[C:20][CH2:21][N:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1)=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8082PiperidineHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 13136250HCID 13136250, compound

Product 1

HCID 13136251HCID 13136251, compoundYield 28.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

156 mg of 6-(3-chloro-1-propinyl)-beta-carboline-3-carboxylic-acid-ethylester is stirred together with 85 mg of piperidine and 76 mg of 1.5-diazabicyclo-[5.4.0]undec-5-ene in 10 ml of absolute ethanol under nitrogen and exclusion of water for 11/2 h at 60° C. After evaporation, the residue is chromatographed on 25 g of silica gel with methylene-chloride/methanol (10/2) as the eluant. 51 mg of 6-[3-(1-piperidinyl)-1-propinyl]-beta-carboline-3-carboxylic-acid-ethylester is obtained.

Workup

  1. custom2 h
  2. customat 60° C
  3. customAfter evaporation
  4. customthe residue is chromatographed on 25 g of silica gel with methylene-chloride/methanol (10/2) as the eluant

Sources & evidence

ORD record
ord-e81c5445080e43c69ee592818c3377b3
Source dataset
uspto-grants-1984_03
Patent number
US04435403

Reaction notes

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