HCID 3485466, compound → HCID 16784866, compound

HRID 1015903Notes

Reaction equation

HRID 1015903 reaction equation
[N:1]1([S:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[C:11]#[N:12])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Ni]>[N:1]1([S:6]([C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH2:11][NH2:12])(=[O:8])=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 3485466HCID 3485466, compound

Product 1

HCID 16784866HCID 16784866, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

(Step 2) A solution of 2-(pyrrolidin-1-ylsulfonyl)benzonitrile obtained in Step 1 (0.1 g) and Raney-nickel (5 mg) in methanol (2.2 ml) was stirred at room temperature for 19 hr under a hydrogen atmosphere (50 psi). The reaction mixture was filtered through celite, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=5:1) to give 1-[2-(pyrrolidin-1-ylsulfonyl)phenyl]methanamine (70 mg).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate→ethyl acetate:methanol=5:1)

Sources & evidence

ORD record
ord-bfbae6b539bb4195b69088df33edf3d6
Source dataset
uspto-grants-2011_07
Patent number
US07985863B2

Reaction notes

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