Pyrrolidine → 3-(2-Pyrrolidinylethyl)-4-chloro-5-methoxyindole

HRID 1898998Notes

Reaction equation

HRID 1898998 reaction equation
[C:1]([CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[C:11]=2[Cl:13])[NH:6][CH:5]=1)#[N:2].N1[CH2:20][CH2:19][CH2:18][CH2:17]1>CO.[Ni]>[N:2]1([CH2:1][CH2:3][C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[C:10]([O:14][CH3:15])[C:11]=3[Cl:13])[NH:6][CH:5]=2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 233730472-(4-Chloro-5-methoxy-1H-indol-3-yl)acetonitrile

Product 1

HCID 572264643-(2-Pyrrolidinylethyl)-4-chloro-5-methoxyindole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

3-Cyanomethyl-4-chloro-5-methoxyindole (2.0 g, 9.1 mmol) was reductively aminated with pyrrolidine (32 ml) in methanol (100 ml) over Raney nickel for 21/2 hours at 30 p.s.i. pressure, at room temperature. After removal of the catalyst, the solvent was removed and the crude mixture purified by chromatography (SiO2 ; CHCl3 /MeOH) to give 3-(2-Pyrrolidinylethyl)-4-chloro-5-methoxyindole (1.26 g) as a solid. Part of this product (250 mg) was dissolved in methanol (10 ml) and treated with a solution of fumaric acid (150 mg) in methanol (5 ml), then ether to give the product as the hemifumarate salt (244 mg), m.p. 217°-8° C.

Workup

  1. custom2 hours
  2. customat room temperature
  3. customAfter removal of the catalyst
  4. customthe solvent was removed
  5. customthe crude mixture purified by chromatography (SiO2 ; CHCl3 /MeOH)

Sources & evidence

ORD record
ord-144f80f0155449bf990f144b917a10c4
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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