Diethylene Glycol → HCID 54552431, compound

HRID 258710Notes

Reaction equation

HRID 258710 reaction equation
[CH:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[CH2:19][C@H:13]3[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C@@H:12]3[CH2:11][C:10](=O)[C:9]=2[CH:21]=1)([CH3:3])[CH3:2].O.NN.[OH-].[K+].C(O)COCCO>O>[CH:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[CH2:19][C@H:13]3[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C@@H:12]3[CH2:11][CH2:10][C:9]=2[CH:21]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 8117Diethylene GlycolHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 54098217HCID 54098217, compound

Product 1

HCID 54552431HCID 54552431, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 25.0 g of trans-1,2,3,4,4a,5,11,11a-octahydro-8-isopropylamino-2-methyl-6H-benzo[5,6]-cyclohepta[1,2-c]pyridin-6-one, 16.0 ml of hydrazine hydrate, 16.0 g of potassium hydroxide and 350 ml of diethylene glycol, is heated first for 1 hour at 150° and then for 3 hours at 200° C., whereby the water formed distils off. The mixture is cooled to room temperature, diluted with water and shaken with methylene chloride. The organic phase is washed neutral with water, dried over sodium sulphate and evaporated, and the residue is reacted in ethanol with the theoretical amount of maleic acid to crystallise out the heading compound in hydrogen maleate form, which is filtered off and recrystallised from ethanol, m.p. from 185° (decomp.).

Workup

  1. temperatureis heated first for 1 hour at 150°
  2. customdistils off
  3. additiondiluted with water
  4. washThe organic phase is washed neutral with water
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. customthe residue is reacted in ethanol with the theoretical amount of maleic acid
  8. customto crystallise out the heading compound in hydrogen maleate form, which
  9. filtrationis filtered off
  10. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-4275cadb88b24d29b44cb4dbd6ddf7e6
Source dataset
uspto-grants-1977_07
Patent number
US04034095

Reaction notes

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