Benzoyl chloride → HCID 18915245, compound

HRID 1017544Notes

Reaction equation

HRID 1017544 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:12]=[CH:11][C:10]2[N:9]([CH3:13])[C:8]3[C:14]4([CH2:20][CH2:21][C:7]=3[C:6]=2[CH:5]=1)[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]4.C(N(CC)CC)C.[C:29](Cl)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCl>[OH2:3].[C:29]([N:17]1[CH2:18][CH2:19][C:14]2([C:8]3[N:9]([CH3:13])[C:10]4[CH:11]=[CH:12][C:4]([O:3][CH3:2])=[CH:5][C:6]=4[C:7]=3[CH2:21][CH2:20]2)[CH2:15][CH2:16]1)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 18403961HCID 18403961, compound

Product 1

HCID 18915245HCID 18915245, compoundYield 125.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1,4-dihydro-7-methoxy-4-methylspiro[cyclopent[b]indole-3(2H), 4′-piperidine] hydrochloride (0.50 g) and triethylamine (0.33 g) in dichloromethane (50 ml) was added benzoyl chloride (0.23 g) at 0° C., under nitrogen, with stirring. The reaction mixture was stirred for 5 hrs at ambient temperature. Dichloromethane (200 ml) was added and the mixture was washed with water and saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated in vacuo. The residue was flash chromatographed (silica gel), eluting with 5% ethyl acetate/dichloromethane. The appropriate fractions were collected and concentrated to give 0.40 g (66%) of product, mp 197-198° C.

Workup

  1. stirringThe reaction mixture was stirred for 5 hrs at ambient temperature
  2. washthe mixture was washed with water and saturated sodium chloride solution
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated in vacuo
  6. customchromatographed (silica gel)
  7. washeluting with 5% ethyl acetate/dichloromethane
  8. customThe appropriate fractions were collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-9a7c7ccdc149426baabb8ce2be25fcc8
Source dataset
uspto-grants-2002_11
Patent number
US06479501B2

Reaction notes

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