Cyclohexanone → HCID 59859849, compound

HRID 1944530Notes

Reaction equation

HRID 1944530 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[C:11]1(=O)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C([BH3-])#N.[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 7967Cyclohexanone2×HCID 34115665-BromoindolineHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 59859849HCID 59859849, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 5-bromo-2,3-dihydro-1H-indole (94.0 g, 20.2 mmol), cyclohexanone (4.6 mL, 44.4 mmol) and sodium cyanoborohydride (1.6 g, 25.5 mmol) in methanol (100 mL) was heated at reflux for 16 hours. More cyclohexanone (2.3 mL, 22.2 mmol) and sodium cyanoborohydride (1.6 g, 25.5 mmol) were added. Heating was continued for 1 day. The solvent was evaporated in vacuo, and the residue was treated with ammonium hydroxide in water. The product was extracted into dichloromethane, and dried over sodium sulfate. The solvent was evaporated in vacuo, and the product was purified by flash silica gel chromatography, eluted with ethyl acetate (1% to 2%) in hexane to give an oil, 7.49 g (37%). MS: m/z 280 (MH+). 1H NMR (CDCl3): 1.08-1.20 (m, 1 H), 1.25-1.42 (m, 4 H), 1.64-1.74 (m, 1 H), 1.76-1.88 (m, 4 H), 2.91 (t, 2 H), 3.24-3.32 (m, 1 H), 3.36 (t, 2 H), 6.23 (d, 1 H) and 7.08-7.11 (m, 2 H).

Workup

  1. temperatureat reflux for 16 hours
  2. temperatureHeating
  3. customThe solvent was evaporated in vacuo
  4. additionthe residue was treated with ammonium hydroxide in water
  5. extractionThe product was extracted into dichloromethane
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe product was purified by flash silica gel chromatography
  9. washeluted with ethyl acetate (1% to 2%) in hexane
  10. customto give an oil, 7.49 g (37%)

Sources & evidence

ORD record
ord-0f0025ecbf764373a8dcd3c68d238e72
Source dataset
uspto-grants-2013_03
Patent number
US08394828B2

Reaction notes

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