Chloroform → HCID 59701391, compound

HRID 902637Notes

Reaction equation

HRID 902637 reaction equation
[Cl:1][C:2]1[C:37]([C:38]([F:41])([F:40])[F:39])=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][N:5]([CH2:20][CH:21]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[C:11]=1[CH3:19].C(Cl)(Cl)Cl>CO.[Pd]>[Cl:1][C:2]1[C:37]([C:38]([F:39])([F:40])[F:41])=[CH:36][CH:35]=[CH:34][C:3]=1[CH2:4][N:5]([CH2:20][CH:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([CH3:19])=[C:12]([NH2:16])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 6212ChloroformHCID 69253779HCID 69253779, compound

Product 1

HCID 59701391HCID 59701391, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-[3-(2-methyl-3-nitro-phenoxy)-propyl]-amine (300 mg, 0.51 mmol) was dissolved in methanol (100 ml), and hydrogenated with 10% Pd/C (40 mg) at 60 psi at room temperature. After 2.5 h, the reaction mixture was filtered and concentrated in vacuo to give an amber oil, 0.25 g (89%). Flash silica gel chromatography (Supelco Discovery DSC-Si) (CHCl3) afforded the title compound as a pure oil (75%). MS (ESI) 552.5 (M−H+).

Workup

  1. customat room temperature
  2. filtrationthe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customto give an amber oil, 0.25 g (89%)

Sources & evidence

ORD record
ord-f1f6294f9c1240189d1eeef0f67f1b26
Source dataset
uspto-grants-2008_04
Patent number
US07365085B2

Reaction notes

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