HCID 58099974, compound → HCID 16778227, compound

HRID 2171322Notes

Reaction equation

HRID 2171322 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>C(O)C.[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 702EthanolSolvent

Procedure

To a flask charged with 10% Pd/C (50 mg) under inert atmosphere was added a solution of 1-(4-nitro-3-(trifluoromethyl)phenyl)pyrrolidine (350 mg, 1.34 mmol) in ethanol. The reaction was stirred under H2 atmosphere for 16 h, then filtered and dried down to provide 4-(pyrrolidin-1-yl)-2-(trifluoromethyl)aniline (300 mg, 97% yield). M+H m/z 231.3. 1H NMR (400.0 MHz, DMSO-d6) δ 6.84 (d, J=8.8 Hz, 1H), 6.72 (dd, J=2.5, 8.8 Hz, 1H), 6.53 (d, J=2.7 Hz, 1H), 4.74 (s, 2H), 3.18 (m, 4H), 1.99-1.95 (m, 4H).

Workup

  1. filtrationfiltered
  2. customdried down

Sources & evidence

ORD record
ord-08658a9cb7b54b2580cc13b6c48d9ac5
Source dataset
uspto-grants-2015_06
Patent number
US09051324B2

Reaction notes

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