Pyridine → HCID 59363368, compound

HRID 905971Notes

Reaction equation

HRID 905971 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].Cl.[CH3:9][CH:10]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][C:11]1=[O:17].N1C=CC=CC=1>C(Cl)Cl>[C:1]([N:14]1[CH2:15][CH2:16][CH:10]([CH3:9])[C:11](=[O:17])[CH2:12][CH2:13]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 673852685-Methylazepan-4-One Hydrochloride

Product 1

HCID 59363368HCID 59363368, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (0.437 mL, 4.62 mmol) was added at 0° C. to a solution of 5-methyl-azepan-4-one hydrochloride (0.740 g, 3.08 mmol) in DCM (20 mL) and pyridine (0.25 mL, 3.08 mmol). The reaction mixture was stirred at RT for 8 hours before being partitioned between DCM and H2O. The organic layer was dried (Na2SO4), filtered, and evaporated. The crude residue was purified by SiO2 chromatography (100% EtOAc) to give 0.220 g of 1-acetyl-5-methyl-azepan-4-one (42% yield).

Workup

  1. custombefore being partitioned between DCM and H2O
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude residue was purified by SiO2 chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-586c668627534a8ba90fa8b694f9e74d
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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