Ethylenediamine → HCID 19747255, compound

HRID 484318Notes

Reaction equation

HRID 484318 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[C:20](=[C:21]3[CH2:26][CH2:25][N:24]([CH2:27][C:28]([O:30]CC)=O)[CH2:23][CH2:22]3)[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH2:13][CH2:12][C:11]=2[CH:33]=1)#[N:6]>O>[C:5]([C:7]1[CH:8]=[CH:9][C:10]2[C:20](=[C:21]3[CH2:22][CH2:23][N:24]([CH2:27][C:28](=[O:30])[NH:3][CH2:2][CH2:1][NH2:4])[CH2:25][CH2:26]3)[C:15]3=[N:16][CH:17]=[CH:18][CH:19]=[C:14]3[CH2:13][CH2:12][C:11]=2[CH:33]=1)#[N:6]

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 54519729HCID 54519729, compound

Product 1

HCID 19747255HCID 19747255, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Ethylenediamine (4 ml) was added to 0.5 g of 8-cyano-11-(1-ethoxycarbonylmethyl-4-piperidylidene)6,11-dihydro-5H-benzo[5,6]-cyclohepta[1,2-b]pyridine, followed by stirring at 70°-80° C. for 3 hours. After the reaction, water was added and the resulting mixture was extracted with ethyl acetate. The extract was dried over anhydrous Na2SO4. The ethyl acetate was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column and, from relevant fractions eluted with chloroform:methanol (20:1 - 10:1), 0.32 g of 8-cyano-11-[1-(2-aminoethylcarbamoylmethyl)-4-piperidylidene]-6,11-dihydro-5H-benzo[5,6]cyclohepta[1,2-b]pyridine was obtained (yield: 62%).

Workup

  1. additionwas added
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous Na2SO4
  4. distillationThe ethyl acetate was distilled off under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column and, from relevant fractions
  6. washeluted with chloroform:methanol (20:1 - 10:1)

Sources & evidence

ORD record
ord-8ef6918b1bcd44c590e77c5bc07bd9d6
Source dataset
uspto-grants-1993_07
Patent number
US05231101

Reaction notes

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