(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole → (R)-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole

HRID 745007Notes

Reaction equation

HRID 745007 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17].[H][H]>C(O)C.[Pd]>[CH3:17][N:13]1[CH2:14][CH2:15][CH2:16][C@@H:12]1[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[CH:2][CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 2

HCID 11185464(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indoleHCID 178418361HCID 178418361, compound

Product 1

HCID 44397420(R)-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indoleYield 65.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(R)-5-Bromo-3-(N-methylpyrrolidin-2-yl-methyl)-1H-indole (60 mg, 0.2 mmol) was dissolved in ethanol (1 mL) and hydrogenated over 10% palladium on carbon (45 mg) at 60 p.s.i. of hydrogen pressure at room temperature for 16 hours. The reaction mixture was evaporated to dryness, and the residue partitioned between ethyl acetate and 10% aqueous sodium carbonate. The organic phase was dried (Na2SO4), and evaporated in vacuo. The resulting residue was purified by column chromatography on silica gel (eluting with 89:10:1 CH2Cl2 :MeOH:NH4OH) to give the title compound (28 mg). Anal. Calcd for C14H18N2 ·1/8 CH2Cl2C,75.42; H,8.18; N,12.46. Found: C,75.50; H,8.51; N,12.09⟦alpha⟧sup.25D =+60.2° (C=0.088, CHCl3).

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. customthe residue partitioned between ethyl acetate and 10% aqueous sodium carbonate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated in vacuo
  5. customThe resulting residue was purified by column chromatography on silica gel (eluting with 89:10:1 CH2Cl2 :MeOH:NH4OH)

Sources & evidence

ORD record
ord-a1cef8e746984606abc1adc7639bc7e4
Source dataset
uspto-grants-1996_09
Patent number
US05559246

Reaction notes

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