Acetic Anhydride → HCID 68408763, compound

HRID 888017Notes

Reaction equation

HRID 888017 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=[O:22])[C:10]1[CH:15]=[CH:14][C:13]([CH:16]2[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]2)=[CH:12][CH:11]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>CN(C)C(=O)C>[C:23]([N:19]1[CH2:20][CH2:21][CH:16]([C:13]2[CH:14]=[CH:15][C:10]([C:9]([NH:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH2:1])=[O:22])=[CH:11][CH:12]=2)[CH2:17][CH2:18]1)(=[O:25])[CH3:24]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 16225584N-(2-Aminophenyl)-4-piperidin-4-ylbenzamide

Product 1

HCID 68408763HCID 68408763, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

N-(2-aminophenyl)-4-piperidin-4-ylbenzamide (Example 5, 30 mg, 0.10 mmol) was stirred and dissolved in N,N-dimethylacetamide (2 ml) and acetic anhydride (0.011 ml, 0.11 mmol) added. The reaction was stirred at ambient temperature for 1 hour and then partitioned between water and ethyl acetate. The organic layer was separated, washed with brine and dried over magnesium sulfate, filtered and evaporated to give the title compound as a colourless solid (23 mg, 68%); NMR Spectrum: (DMSO-d6) 1.48 (m, 1H), 1.64 (m, 1H), 1.79 (m, 2H), 2.02 (s, 3H), 2.59 (m, 1H), 2.84 (m, 1H), 3.13 (m, 1H), 3.92 (d, 1H), 4.53 (d, 1H), 4.85 (s, 2H), 6.58 (m, 1H), 6.76 (d, 1H), 6.95 (m, 1H), 7.15 (d, 1H), 7.37 (d, 2H), 7.90 (d, 2H), 9.55 (s, 1H); Mass Spectrum: M+H+ 338.

Workup

  1. custompartitioned between water and ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-acd2004a7f414ae59a7f45fe7a22be70
Source dataset
uspto-grants-2012_08
Patent number
US08247562B2

Reaction notes

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