Potassium Carbonate → HCID 17829512, compound

HRID 1743404Notes

Reaction equation

HRID 1743404 reaction equation
I[CH2:2][C:3]1([CH3:19])[O:14][C:13]2[C:5](=[C:6]3[C:10](=[C:11]([CH3:16])[C:12]=2[CH3:15])[NH:9][C:8]([CH3:18])([CH3:17])[CH2:7]3)[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:14][C:13]2[C:5](=[C:6]3[C:10](=[C:11]([CH3:16])[C:12]=2[CH3:15])[NH:9][C:8]([CH3:18])([CH3:17])[CH2:7]3)[CH2:4]1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 14002432,3,4,5-Tetrahydro-1H-benzo(d)azepineHCID 9929328HCID 9929328, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 17829512HCID 17829512, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
180 °C

Procedure

A suspension of 1,6,7,8-tetrahydro-2-(iodomethyl)-2,4,5,7,7-pentamethyl-2H-furo[3,2-e]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 at 180° C. for 3 hours under the nitrogen atmosphere. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate two times, The combined organic layers were 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 10:1) to obtain an oil. This was dissolved in methanol, a 10% hydrogen chloride-methanol solution was added to obtain 464 mg of the title compound.

Workup

  1. extractionthe mixture was extracted with ethyl acetate two times
  2. washThe combined organic layers were washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto obtain an oil

Sources & evidence

ORD record
ord-99a9e0793f7c4bd684dd1093e07feb0a
Source dataset
uspto-grants-2006_03
Patent number
US07008940B1

Reaction notes

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