Diisopropylethylamine → HCID 13136253, compound

HRID 1982462Notes

Reaction equation

HRID 1982462 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]([NH2:20])=[CH:13][CH:12]=3)=[O:5])[CH3:2].Cl/[CH:22]=[CH:23]\[CH2:24][CH2:25]Cl.C(N(C(C)C)C(C)C)C>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[C:18]=1[CH3:19])=[CH:15][C:14]([N:20]1[CH:25]=[CH:24][CH:23]=[CH:22]1)=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 130373386-Amino-4-methyl-beta-carboline-3-carboxylic-acid-ethylesterHCID 86614758HCID 86614758, compound

Product 1

HCID 13136253HCID 13136253, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3.25 g of 6-amino-4-methyl-beta-carboline-3-carboxylic-acid-ethylester in 70 ml of ethanol, together with 1.7 ml of 1,4-dichloro-2-cis-butene and 4.5 g of ethyldiisopropylamine is heated for 10 h at 50° C. After stirring in 250 ml of ice water, the precipitate is filtered, washed and dried in vacuum. The raw product (3.4 g of a mixture of dihydropyrrole derivative and pyrrole derivative) is dissolved in 600 ml of methylene chloride and, after addition of 17 g of pyrolusite, is stirred for 2 h at room temperature. After filtering, and distilling off the solvent, 2.75 g of raw product is obtained crystallizing out of acetone. In this manner, 2.13 g of 4-methyl-6-(1-pyrrolyl)-beta-carboline-3-carboxylic-acid-ethylester with a m.p. of 214°-217° C. is obtained.

Workup

  1. filtrationthe precipitate is filtered
  2. washwashed
  3. customdried in vacuum
  4. dissolutionThe raw product (3.4 g of a mixture of dihydropyrrole derivative and pyrrole derivative) is dissolved in 600 ml of methylene chloride
  5. additionafter addition of 17 g of pyrolusite
  6. filtrationAfter filtering
  7. distillationdistilling off the solvent
  8. custom2.75 g of raw product is obtained
  9. customcrystallizing out of acetone

Sources & evidence

ORD record
ord-12f5a57adc97483f8e047a929e9b7245
Source dataset
uspto-grants-1986_06
Patent number
US04596808

Reaction notes

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