1-(2-(4-Nitrophenoxy)ethyl)pyrrolidine → 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline

HRID 1876887

Reaction equation

HRID 1876887 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([O:8][CH2:9][CH2:10][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:6][CH:5]=1)([O-])=O.[H][H]>CO.[Pd]>[N:11]1([CH2:10][CH2:9][O:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:17][CH:16]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 4198581-(2-(4-Nitrophenoxy)ethyl)pyrrolidineHCID 178418361HCID 178418361, compound

Product 1

HCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[2-(4-nitrophenoxy)ethyl]pyrrolidine (from Combi-Blocks, LLC, 5.00 g, 0.0212 mol) in 100 mL of MeOH was hydrogenated in the presence of 0.5 g 10% Pd/C, under balloon pressure of hydrogen, overnight. After filtering off the catalyst, the filtrate was evaporated to dryness and used directly in next step (4.36 g, 99.88%). LCMS (M+H) 207.4.

Workup

  1. filtrationAfter filtering off the catalyst
  2. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-d9bda850dfd74ef182f43c6f143b8063
Source dataset
uspto-grants-2012_11
Patent number
US08309718B2

Linked notes

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