Acetic Anhydride → HCID 66571464, compound

HRID 83642Notes

Reaction equation

HRID 83642 reaction equation
[CH2:1]([N:8]([CH3:28])[C:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:31](OC(=O)C)(=[O:33])[CH3:32]>CN(C=O)C.[Cl-].[NH4+].C(OCC)(=O)C>[C:31]([N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[C:19]1[C:17]([N:14]1[CH2:15][CH2:16][CH:11]([C:9]([N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH3:28])=[O:10])[CH2:12][CH2:13]1)=[O:18])(=[O:33])[CH3:32]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 24758Sodium hydrideHCID 66571403N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide

Product 1

HCID 66571464HCID 66571464, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
80 °C

Procedure

A solution of N-benzyl-1-(1H-indole-2-carbonyl)-N-methylpiperidine-4-carboxamide (100 mg, 0.266 mmol) in 1 mL of DMF was added to a suspension of sodium hydride (11.72 mg, 0.293 mmol) in 2.0 mL DMF. The reaction was stirred at 80° C. for 10 minutes before adding acetic anhydride (0.050 ml, 0.533 mmol). The reaction was allowed to stir for 5 hours before it was cooled to room temperature and diluted with ammonium chloride and ethyl acetate. The organic phase was washed with saturated ammonium chloride twice, followed by saturated sodium chloride, dried over magnesium sulfate, filtered and concentrated. The crude material was purified via silica gel chromatography for 50% ethyl acetate/hexanes to 100% ethyl acetate. Purification afforded white solid as the product. (Yield: 13 mg, white solid) 1H-NMR (400 MHz, DMSO-d6) 8.12-8.06, 7.65-7.59, 7.41-7.13, 6.91-6.84, 4.65, 4.49, 3.96-3.83, 3.06-2.94, 2.76, 2.61-2.55, 1.87-1.49

Workup

  1. stirringto stir for 5 hours before it
  2. temperaturewas cooled to room temperature
  3. washThe organic phase was washed with saturated ammonium chloride twice
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified via silica gel chromatography for 50% ethyl acetate/hexanes to 100% ethyl acetate
  8. customPurification
  9. customafforded white solid as the product

Sources & evidence

ORD record
ord-06f7435718b94ed3acb8e57805668165
Source dataset
uspto-grants-2014_09
Patent number
US08846684B2

Reaction notes

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