Triethylamine → HCID 22611406, compound

HRID 843875Notes

Reaction equation

HRID 843875 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1.C(N(CC)CC)C.[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[C:35](Cl)=[O:36].[OH-].[Na+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[CH:25]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27][C:26]=1[C:35]([NH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH:11]1[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]1)=[O:36]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 752462-Naphthoyl chlorideHCID 118312203-(1-Methylpiperidin-4-yl)-1h-indol-5-amine

Product 1

HCID 22611406HCID 22611406, compoundYield 82.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.989 gm (4.31 mMol) 5-amino-3-(1-methylpiperidin-4-yl)-1H-indole in 20 mL tetrahydrofuran and 10 mL dimethylformamide were added 0.721 mL (5.2 mMol) triethylamine followed by 0.904 gm (4.74 mMol) 2-naphthoyl chloride. After 18 hours the reaction mixture was cooled in an ice bath and then diluted with 100 mL ethyl acetate followed by 50 mL 2N sodium hydroxide. The phases were separated and the aqueous extracted with ethyl acetate. The organic extracts were combined then washed sequentially with 2N sodium hydroxide, water and saturated aqueous sodium chloride. The remaining organics were dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to flash chromatography, eluting with 100:10:1 dichloromethane:methanol:ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure. The residue was precipitated from ethyl acetate/hexane to give 1.355 gm (82.1%) of the title compound as a tan powder.

Workup

  1. temperatureAfter 18 hours the reaction mixture was cooled in an ice bath
  2. customThe phases were separated
  3. extractionthe aqueous extracted with ethyl acetate
  4. washThe organic extracts were combined then washed sequentially with 2N sodium hydroxide, water and saturated aqueous sodium chloride
  5. dry with materialThe remaining organics were dried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluting with 100:10:1 dichloromethane
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was precipitated from ethyl acetate/hexane

Sources & evidence

ORD record
ord-0b83a681f11940fa8a825e43611ca3f6
Source dataset
uspto-grants-2002_04
Patent number
US06380201B1

Reaction notes

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