Potassium Hydroxide → HCID 14181206, compound

HRID 2351468Notes

Reaction equation

HRID 2351468 reaction equation
[CH2:1]([N:4]([CH2:20][CH2:21][CH3:22])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:15][NH:16]C(=O)C)[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:2][CH3:3].[OH-].[K+]>C(O)C>[CH2:20]([N:4]([CH2:1][CH2:2][CH3:3])[CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[C:8]([CH2:15][NH2:16])[CH:9]=[CH:10][CH:11]=2)[CH2:6]1)[CH2:21][CH3:22]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 14181205HCID 14181205, compound

Product 1

HCID 14181206HCID 14181206, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

10.6 g (35 mmol) of 2-dipropylamino-8-acetamidomethyl-1,2,3,4-tetrahydronaphthalene in 100 ml of ethanol and 23.1 g (350 mmol) of potassium hydroxide were heated to a gentle reflux for 24 h at 90° C. under nitrogen. The batch was subsequently stirred into 1 liter of ice water and the mixture was extracted with dichloromethane. The organic phase was washed with water and dried over sodium sulphate. The solvent was removed by distillation in vacuo. The reaction product, remaining as a residue, was purified by column chromatography on silica gel using methanol/triethylamine, 95:5, as eluent.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe organic phase was washed with water
  3. dry with materialdried over sodium sulphate
  4. customThe solvent was removed by distillation in vacuo
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f17868ce30fa4519a3e74bde287480b9
Source dataset
uspto-grants-1989_10
Patent number
US04873262

Reaction notes

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