Nitrogen → 4-Pentafluoroethyl-3-(2-pyrrolidin-1-yl-ethoxy)-phenylamine

HRID 491615Notes

Reaction equation

HRID 491615 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])=[C:8]([CH:17]=1)[O:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)([O-])=O.N#N>[Pd].CO>[F:24][C:18]([F:23])([C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:17][C:8]=1[O:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)[C:19]([F:22])([F:21])[F:20]

Participants

5

Reactant 2

HCID 947NitrogenHCID 865946891-[2-(5-Nitro-2-pentafluoroethylphenoxy)-ethyl]-pyrrolidine

Product 1

HCID 860022324-Pentafluoroethyl-3-(2-pyrrolidin-1-yl-ethoxy)-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A flask was charged with 1-[-(5-nitro-2-pentafluoroethyl-phenoxy)-ethyl]-pyrrolidine (Step A) (1.8 g) and MeOH (25 mL) and placed under argon. Pd/C was added carefully and the atmosphere was replaced with H2. The reaction was stirred for 2.5 days at RT. The reaction mixture was blanketed with N2, filtered through a pad of Celite® and evaporated. The reaction mixture was taken up in a small amount of acetone, and filtered through a plug of silica gel using 90:10:1 (CH2Cl2:MeOH:NH4OH) as the eluant. The title compound was isolated as a yellow solid.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. customevaporated
  3. filtrationfiltered through a plug of silica gel using 90:10:1 (CH2Cl2:MeOH:NH4OH) as the eluant

Sources & evidence

ORD record
ord-be1ee7d62240422b93b26005ed8f4e93
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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