Potassium Hydroxide → HCID 18677423, compound

HRID 380377Notes

Reaction equation

HRID 380377 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][NH:18]C(=O)OCC)[CH2:14][C:5]=3[C:4]=2[CH:3]=1.[OH-].[K+]>CC(O)C>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH2:15][CH2:16][CH2:17][NH2:18])[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 86585567HCID 86585567, compound

Product 1

HCID 18677423HCID 18677423, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of intermediate (10) (0.063 mol) and KOH (35 g) in 2-propanol (300 ml) was stirred and refluxed overnight. The solvent was evaporated. The residue was stirred in water and this mixture was extracted with methyl isobutyl ketone. The separated organic layer was dried, filtered and the solvent evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 85/15). The pure fractions were collected and the solvent was evaporated, yielding 7 g (46%) of 1,3,4,5-tetrahydro-8-methyl-2H-pyrido[4,3-b]indole-2-propanamine (intermediate 11).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was evaporated
  3. stirringThe residue was stirred in water
  4. extractionthis mixture was extracted with methyl isobutyl ketone
  5. customThe separated organic layer was dried
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 85/15)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4cc4454eb83c4f4bb997db7a4cac9058
Source dataset
uspto-grants-2001_10
Patent number
US06303614B1

Reaction notes

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