Hydrogen Peroxide → 3-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-benzamide

HRID 1827943Notes

Reaction equation

HRID 1827943 reaction equation
[CH2:1]([N:8]1[CH2:15][CH2:14][C:13]2([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]#[N:21])[CH2:16][CH:9]1[CH2:10][CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-:26].[K+].[K+].OO>CS(C)=O>[CH2:1]([N:8]1[CH2:15][CH2:14][C:13]2([C:17]3[CH:18]=[C:19]([CH:22]=[CH:23][CH:24]=3)[C:20]([NH2:21])=[O:26])[CH2:16][CH:9]1[CH2:10][CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 784Hydrogen Peroxide2×HCID 11430Potassium Carbonate2×HCID 220645903-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-benzonitrile

Product 1

HCID 220645623-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

3-(2-Benzyl-2-aza-bicyclo[3.3.1]non-5-yl)-benzonitrile (1.95 g, 6.16 mmol) in DMSO (55 ml) was charged with potassium carbonate (120 mg, 0.86 mmol) then 30% aqueous hydrogen peroxide (3.2 ml, 30.8 mmol). The reaction mixture was allowed to stir at room temperature for 23 h at which time it was determined not to have proceeded. Additional potassium carbonate (850 mg, 6.16 mmol) and 30% aqueous hydrogen peroxide (6.4 ml, 61.6 mmol) were introduced and stirred for 5.5 h. After a water quench (50 ml), the product was extracted with EtOAc (3×50 ml), washed with 50% saturated aqueous NaCl solution (5×50 ml), dried over Na2SO4, filtered and concentrated to a white solid which was triturated with hexanes and collected (1.0 g, 49%). (TLC 50% EtOAc/hexanes Rf 0.08); 1H NMR (400 MHz, CDCl3) δ 7.83–7.85 (m, 1H), 7.49–7.57 (m, 1H), 7.40–7.47 (m, 1H), 7.38–7.28 (m, 5H), 7.21–7.25 (m, 1H), 6.10 (brs, 1H), 5.63 (brs, 1H); 3.74–3.82 (m, 2H), 3.06–3.15 (m, 2H), 2.86–2.96 (m, 1H), 2.16–2.26 (m, 2H), 1.96–2.08 (m, 4H), 1.84–1.89 (m, 1H), 1.68–1.74 (m, 1H), 1.59–1.65 (m, 1H), 1.34–1.42 (m, 1H); APCI MS m/z 335.1 (M+1)+.

Workup

  1. stirringstirred for 5.5 h
  2. customAfter a water quench (50 ml)
  3. extractionthe product was extracted with EtOAc (3×50 ml)
  4. washwashed with 50% saturated aqueous NaCl solution (5×50 ml)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to a white solid which
  8. customwas triturated with hexanes
  9. customcollected (1.0 g, 49%)

Sources & evidence

ORD record
ord-78f0809ca21547509fd74656053eecba
Source dataset
uspto-grants-2006_06
Patent number
US07056930B2

Reaction notes

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