Potassium Hydroxide → HCID 19773374, compound

HRID 1614269Notes

Reaction equation

HRID 1614269 reaction equation
[ClH:1].[C:2]([N:5]([C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH:11]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:12]2)C)(=O)C.[OH-].[K+]>C(O)COCCO.O>[ClH:1].[ClH:1].[CH3:2][NH:5][C:7]1[CH:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH2:9][CH2:10][CH:11]([NH:17][CH2:18][CH2:19][CH3:20])[CH2:12]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 19773377HCID 19773377, compound

Product 1

HCID 19773374HCID 19773374, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Procedure

0.50 g (1.92 mmol) of 5-(N-acetyl-N-methyl-amino)-2-n-propylamino-tetraline-hydrochloride (Example 4.7.8) are stirred with 12.5 g (0.22 mol) of potassium hydroxide in 40 ml of diethyleneglycol for 24 hours at 150° C. The mixture is then cooled, diluted with 400 ml of water and extracted three times with ethyl acetate (50, 15 and 15 ml). The combined extracts are washed with 20 ml of water, dried with sodium sulphate and, after the drying agent has been filtered off, concentrated by rotary evaporation, finally at 80° C. under a complete water-jet vacuum. The residue is crystallised as the hydrochloride analogously to Example 4.1.1. The title compound is obtained in a yield of 0.39 g (69.7% of theory) and with a melting point of 245° C. which does not change when recrystallised from ethanol/ether.

Workup

  1. temperatureThe mixture is then cooled
  2. extractionextracted three times with ethyl acetate (50, 15 and 15 ml)
  3. washThe combined extracts are washed with 20 ml of water
  4. dry with materialdried with sodium sulphate
  5. filtrationafter the drying agent has been filtered off
  6. concentrationconcentrated by rotary evaporation, finally at 80° C. under a complete water-jet vacuum
  7. customThe residue is crystallised as the hydrochloride analogously to Example 4.1.1

Sources & evidence

ORD record
ord-7076de5ae49f4a588daaeb896366d1d9
Source dataset
uspto-grants-1993_03
Patent number
US05196454

Reaction notes

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