HCID 58099974, compound → HCID 16778227, compound

HRID 1805136Notes

Reaction equation

HRID 1805136 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:6][C:5]=1[C:15]([F:18])([F:17])[F:16])([O-])=O>CO.[Pd]>[N:10]1([C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[C:5]([C:15]([F:16])([F:17])[F:18])[CH:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 58099974HCID 58099974, compound

Product 1

HCID 16778227HCID 16778227, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (350 mg, 1.34 mmol) in methanol (2 mL) and Pd/C (30 mg, 0.3 mmol) were stirred for 16 h under H2. The reaction mixture was filtered and the solvent evaporated in vacuo to provide 4-(pyrrolidin-1-yl)-2-(trifluoromethyl)aniline (0.3 g, 97%). LC/MS: m/z 231.3 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 6.84 (d, J=8.8 Hz, 1H), 6.72 (dd, J=8.8, 2.5 Hz, 1H), 6.53 (d, J=2.7 Hz, 1H), 4.74 (s, 2H), 3.21-3.11 (m, 4H), 2.00-1.93 (m, 4H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f122c586ddb44c279ece8cee1d0377ca
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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