Acetic Anhydride → HCID 25104295, compound

HRID 238547Notes

Reaction equation

HRID 238547 reaction equation
Cl.[CH3:2][N:3]([CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)[C:4]([C:6]1[CH:14]=[CH:13][C:9]2=[N:10][O:11][N:12]=[C:8]2[CH:7]=1)=[O:5].[C:21](OC(=O)C)(=[O:23])[CH3:22].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:21]([N:18]1[CH2:19][CH2:20][CH:15]([N:3]([CH3:2])[C:4]([C:6]2[CH:14]=[CH:13][C:9]3=[N:10][O:11][N:12]=[C:8]3[CH:7]=2)=[O:5])[CH2:16][CH2:17]1)(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 25104291HCID 25104291, compound

Product 1

HCID 25104295HCID 25104295, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

N-Methyl-N-piperidin-4-yl-[2,1,3]-benzoxadiazole-5-carboxamide hydrochloride (0.58 g, 1.9 mmol) was suspended in chloroform (50 ml), and acetic anhydride (2 ml) and triethylamine (4 ml), were added. After stirring for 1 h, the mixture was washed with water (100 ml) and H2SO4 (→pH 2) and NaHCO3 solution (100 ml). The aqueous was extracted with chloroform (2×100 ml) and the combined organics dried (MgSO4) and concentrated under vacuum. The residue was purified by silica gel chromatography eluting with ethyl acetate/chloroform/methanol (50:45:5) to give a white solid after crystallization from ethyl acetate/MTBE/hexane (470 mg). Mp=173-175° C., 1H NMR (300 MHz, CDCl3) δ 7.93 (d, J=9.0 Hz, 1H); 7.85 (s, 1H); 7.42 (d, J=9.0 Hz, 1H); 4.90-4.70 and 4.05-3.80 (m, 5H); 2.89 (sb, 3H); 2.13 (sb, 3H), 1.95-1.60 ppm (m, 4H).

Workup

  1. washthe mixture was washed with water (100 ml) and H2SO4 (→pH 2) and NaHCO3 solution (100 ml)
  2. extractionThe aqueous was extracted with chloroform (2×100 ml)
  3. dry with materialthe combined organics dried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with ethyl acetate/chloroform/methanol (50:45:5)
  7. customto give a white solid
  8. customafter crystallization from ethyl acetate/MTBE/hexane (470 mg)

Sources & evidence

ORD record
ord-c3df16f98dd140cb9f70570529891660
Source dataset
uspto-grants-2014_02
Patent number
US08642633B2

Reaction notes

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