Potassium Carbonate → HCID 69739368, compound

HRID 985603Notes

Reaction equation

HRID 985603 reaction equation
I[CH2:2][C:3]1([CH3:19])[O:18][C:6]2=[C:7]([CH3:17])[C:8]3[CH2:9][C:10]([CH3:16])([CH3:15])[NH:11][C:12]=3[C:13]([CH3:14])=[C:5]2[CH2:4]1.[CH2:20]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[CH2:24][CH2:23][NH:22][CH2:21]1.C(=O)([O-])[O-].[K+].[K+].[ClH:37].CO>CN(C)C(=O)C.CO.O>[ClH:37].[CH3:19][C:3]1([CH2:2][CH:24]2[CH2:25][CH2:30][C:29]3[CH:28]=[CH:27][CH:26]=[CH:20][C:21]=3[NH:22][CH2:23]2)[O:18][C:6]2=[C:7]([CH3:17])[C:8]3[CH2:9][C:10]([CH3:16])([CH3:15])[NH:11][C:12]=3[C:13]([CH3:14])=[C:5]2[CH2:4]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepineHCID 21893726Hydrochloride methanolHCID 22506876HCID 22506876, compound

Product 1

HCID 69739368HCID 69739368, compoundYield 45%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of 3,5,6,7-tetrahydro-2-(iodomethyl)-2,4,6,6,8-pentamethyl-2H-furo[2,3-f]indole (520 mg, 1.40 mmol), 2,3,4,5-tetrahydro-1H-3-benzazepine (309 mg, 2.10 mmol) and potassium carbonate (387 mg, 2.80 mmol) in N,N-dimethylacetamide (3 ml) was stirred for 3.5 hours at 180° C. under nitrogen atmosphere. Water was added to the reaction mixture and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with water and saturated brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was subjected to basic silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain an oil. The oil was dissolved in methanol and combined with 10% hydrogen chloride-methanol solution (1.5 ml), and concentrated under reduced pressure. The residue was crystallized from methanol-diisopropyl ether to obtain 269 mg of the title compound.

Workup

  1. extractionthe mixture was extracted twice with ethyl acetate
  2. washwashed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto obtain an oil
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-9f9d49aa1cca451fa8a5815fa0950a34
Source dataset
uspto-grants-2005_03
Patent number
US06872718B1

Reaction notes

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