HCID 15871341, compound → HCID 19600449, compound

HRID 609738Notes

Reaction equation

HRID 609738 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[C:10]3[CH2:16][CH2:17][N:18]([CH3:20])[CH3:19])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[CH:1]1([C:7]2[CH:8]=[C:9]3[C:13](=[CH:14][CH:15]=2)[NH:12][CH:11]=[C:10]3[CH2:16][CH2:17][N:18]([CH3:19])[CH3:20])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 15871341HCID 15871341, compound

Product 1

HCID 19600449HCID 19600449, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-(Cyclohex-1-en-1-yl)-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (Example 9a, 8.4 mg, 0.031 mmol) in ethyl acetate (2 mL) containing a spatula tip of Pd/C (10%) was stirred at room temperature under an atmosphere of hydrogen for 5 h. The crude product was filtered through celite using 10% 2M methanolic ammonia in dichloromethane to rinse. Evaporation of the solvent in vacuo yielded 5-cyclohexyl-3-[2-(N,N-dimethylamino)ethyl]-1H-indole (6.8 mg, 81%); HRMS-FAB+ for C18H26N2 :calculated MH+ :271.21744; found MH+ :271.21692.

Workup

  1. filtrationThe crude product was filtered through celite
  2. washto rinse
  3. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-1e1a2303d4e642969db9a30fa24a9ecc
Source dataset
uspto-grants-1999_12
Patent number
US05998438

Reaction notes

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