Potassium Carbonate → HCID 178465800, compound

HRID 365402Notes

Reaction equation

HRID 365402 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH3:20])[C@H:14]1[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13]1)[N:8]=[C:7]2[C:21]1[CH:22]=[CH:23][C:24](Cl)=[N:25][CH:26]=1)[CH3:2].C(=O)([O-])[O-:29].[K+].[K+].[OH-].[K+].COCCOCCN(CCOCCOC)CCOCCOC>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][CH3:20])[C@H:14]1[C@H:9]([CH2:10][CH2:11][CH2:12][CH2:13]1)[N:8]=[C:7]2[C:21]1[CH:22]=[CH:23][C:24]([OH:29])=[N:25][CH:26]=1)[CH3:2]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 86755875HCID 86755875, compound

Product 1

HCID 178465800HCID 178465800, compoundYield 12.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

850 mg of (+/-)-cis-8,9-diethoxy-6-(2-chloropyrid-5-yl)-1,2,3,4,4a,10b-hexahydrophenanthridine are suspended in 60 ml of toluene, treated with 1.0 g of potassium carbonate, 2.0 g of potassium hydroxide and 0.26 mg of tris[2-(2-methoxyethoxy)ethyl]amine and refluxed overnight. The suspension is filtered, the solvent is removed in vacuo, the residue is taken up in water, and the mixture is neutralized with 0.1 M hydrochloric acid and extracted with ethyl acetate. The organic phase is dried using sodium sulfate, the solvent is removed in vacuo, and the precipitate which is deposited in the course of this is filtered off with suction and dried. M.p.: 211-213° C., yield 12.3% of theory.

Workup

  1. temperaturerefluxed overnight
  2. filtrationThe suspension is filtered
  3. customthe solvent is removed in vacuo
  4. extractionextracted with ethyl acetate
  5. customThe organic phase is dried
  6. customthe solvent is removed in vacuo
  7. filtrationthis is filtered off with suction
  8. customdried

Sources & evidence

ORD record
ord-8a8960743f1d4dd3be2c68f5a9841360
Source dataset
uspto-grants-2000_10
Patent number
US06127378

Reaction notes

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