Hydrogen Peroxide → 4-[4-(2-Benzylamino-ethyl)-phenoxy]-2-chloro-benzamide

HRID 130721Notes

Reaction equation

HRID 130721 reaction equation
C(OC(=O)[N:7]([CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]#[N:24])=[C:19]([Cl:25])[CH:18]=2)=[CH:12][CH:11]=1)(C)(C)C.OO.C([O-])([O-])=[O:37].[K+].[K+].FC(F)(F)C(O)=O>CS(C)=O.C(Cl)Cl>[CH2:26]([NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([NH2:24])=[O:37])=[C:19]([Cl:25])[CH:18]=2)=[CH:12][CH:11]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59729914Benzyl-{2-[4-(3-chloro-4-cyano-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 597301314-[4-(2-Benzylamino-ethyl)-phenoxy]-2-chloro-benzamideYield 149.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

Combine the compound of step 1 (95 mg, 0.21 mmol), H2O2 (25 μl) and K2CO3 (15 mg, 0.10 mmol) in DMSO (0.8 mL), and stir the mixture at room temperature overnight. Add water and extract the aqueous layer with EtOAc. Dry the organic layer over Na2SO4 and eliminate the solvent. Purify by flash chromatography (EtOAc/hexane 50/50) to give a yellow oil. Dissolve the oil in CH2Cl2 (3 mL) and add trifluoroacetic acid (240 μL), and stir the mixture at room temperature for 4 hour. Eliminate the solvent. Purify by an SCX column to give the title compound (57 mg, 76%). Electrospray MS M+1 ion=381. 1H-NMR (CDCl3, 400 MHz): 7.82 (d, 1H, J=8.5 Hz), 7.35-7.20 (m, 7H), 6.99-6.95 (m, 3H), 6.90 (dd, 1H, J=2.5 and 8.5 Hz), 6.53 (m, 2H), 3.83 (s, 2H), 2.95-2.89 (m, 2H), 2.86-2.81 (m, 2H).

Workup

  1. extractionAdd water and extract the aqueous layer with EtOAc
  2. dry with materialDry the organic layer over Na2SO4
  3. customPurify by flash chromatography (EtOAc/hexane 50/50)
  4. customto give a yellow oil
  5. customPurify by an SCX column

Sources & evidence

ORD record
ord-41553e654d674f76847ae2a4c8e77b02
Source dataset
uspto-grants-2008_06
Patent number
US07381719B2

Reaction notes

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