1-[2-(2-Fluoro-4-nitrophenoxy)ethyl]pyrrolidine → 3-Fluoro-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

HRID 409674Notes

Reaction equation

HRID 409674 reaction equation
[F:1][C:2]1[CH:15]=[C:14]([N+:16]([O-])=O)[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1>[Pd].CCO>[F:1][C:2]1[CH:15]=[C:14]([NH2:16])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][CH2:6][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

4

Reactant 1

HCID 252487661-[2-(2-Fluoro-4-nitrophenoxy)ethyl]pyrrolidine

Product 1

HCID 196272463-Fluoro-4-(2-(pyrrolidin-1-yl)ethoxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A suspension of 1-[2-(2-fluoro-4-nitro-phenoxy)-ethyl]-pyrrolidine (1.25 g, 4.92 mmol) and 10% palladium on carbon (0.2 g) in EtOH (20 mL) is stirred for 1 h at RT, under a hydrogen atmosphere. The reaction mixture is filtered through a pad of celite and concentrated to afford the title compound as a brown oil: ESI-MS: 225.1 [MH]+; tR=0.80 min (system 1).

Workup

  1. filtrationThe reaction mixture is filtered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-0a0a33a4d7d04438b138b487fe949116
Source dataset
uspto-grants-2014_06
Patent number
US08759517B2

Reaction notes

Loading…