Benzoyl chloride → HCID 10131568, compound

HRID 1017541Notes

Reaction equation

HRID 1017541 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([C:11]3[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:10]=3[CH2:9][CH2:8]2)[CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].[C:25](Cl)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(OCC)(=O)C>C(#N)C>[C:25]([N:2]1[CH2:3][CH2:4][C:5]2([C:11]3[NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=4[C:10]=3[CH2:9][CH2:8]2)[CH2:6][CH2:7]1)(=[O:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 18915246HCID 18915246, compound

Product 1

HCID 10131568HCID 10131568, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 1,4-dihydrospiro[cyclopent[b]indole-3(2H), 4′-pipendine] hydrochloride (1.0 g) and potassium carbonate (0.8 g) in acetonitrile (10 ml) was added benzoyl chloride (0.5 g), under nitrogen, with stirring. The reaction mixture was heated under reflux for 5 hrs and allowed to cool to ambient temperature. Ethyl acetate (200 ml) was added, and the mixture was washed with water and saturated sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered and the filtrate was concentrated in vacua. The residue was flash chromatographed (silica gel), eluting with 0.5% methanol/dichloromethane. The appropriate fractions were collected and concentrated to give 0.40 g (33%) of product, mp 231-232° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. washthe mixture was washed with water and saturated sodium hydroxide solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated in vacua
  7. customchromatographed (silica gel)
  8. washeluting with 0.5% methanol/dichloromethane
  9. customThe appropriate fractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-0bccb98b2ba14d22ac8cf41a99ef8ed3
Source dataset
uspto-grants-2002_11
Patent number
US06479501B2

Reaction notes

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