Acetic Acid → HCID 18398766, compound

HRID 1018919Notes

Reaction equation

HRID 1018919 reaction equation
[CH3:1][C:2]([CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][CH:6]=1)=O.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[N:14]1([CH:2]([CH3:1])[CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][CH:6]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 8082PiperidineHCID 709893-IndolylacetoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 18398766HCID 18398766, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of indole-3-acetone (5.0 g, 29 mmol) in anhydrous 1,2-dichloroethane (100 ml) under an atmosphere of nitrogen was added piperidine (2.9 ml, 29 mmol), and glacial acetic acid (1.66 ml, 29 mmol) followed by sodium triacetoxyborohydride (6.8 g, 32 mmol). On complete addition the reaction mixture was stirred at room temperature for 17 hours. The mixture was basified by the addition of a saturated solution of sodium hydrogen carbonate, the layers were separated and the organic layer dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The residue was purified by column chromatography on silica elution with 5% CH3OH in CH2Cl2+0.5% 0.88 ammonia to give the title product (3 g, 43%); δH (360 MHz; CDCl3) 0.99 (3H, d, J 6.5 Hz, —CH3), 1.43-1.51 (2H, m, aliphatics), 1.60-1.69 (4H, m, aliphatics), 2.56-2.70 (5H, m, aliphatics+indole CHACHB), 2.87-2.99 (1H, m, indole CHAHBCH (piperidine)), 3.12 (1H, dd, J 13.9 and 3.6 Hz, indole CHACHB), 7.02 (1H, d, J 1.9 Hz, indole H2), 7.09 (1H, m, indole H6), 7.17 (1H, m, indole H5), 7.34 (1H, d, J 8.0 Hz, indole H7), 7.61 (1H, d, J 7.6 Hz, indole H4), 8.01 (1H, bs, indole NH); m/z (ES+) 243 (M++H, 100%).

Workup

  1. additionOn complete addition the reaction mixture
  2. customthe layers were separated
  3. dry with materialthe organic layer dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica elution with 5% CH3OH in CH2Cl2+0.5% 0.88 ammonia

Sources & evidence

ORD record
ord-52fcc13571264d78b85c7ab5a9c6139c
Source dataset
uspto-grants-2002_11
Patent number
US06486153B1

Reaction notes

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