Acetyl chloride → Methyl 3-(1-acetylpiperidin-2-yl)-5-(1-cyclohexylethyl)benzoate

HRID 1175212Notes

Reaction equation

HRID 1175212 reaction equation
[C:1]1([C:7]([C:9]2[CH:10]=[C:11]([CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=3)[CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[C:34](Cl)(=[O:36])[CH3:35]>C(O)C.Cl.C(Cl)Cl.O=[Pt]=O>[C:34]([N:20]1[CH2:21][CH2:22][CH2:23][CH2:24][CH:19]1[C:17]1[CH:16]=[C:11]([CH:10]=[C:9]([CH:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[CH3:8])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])(=[O:36])[CH3:35]

Participants

8

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68688416HCID 68688416, compound

Product 1

HCID 68688722Methyl 3-(1-acetylpiperidin-2-yl)-5-(1-cyclohexylethyl)benzoate

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To an argon purged solution of methyl 3-(1-phenylvinyl)-5-(pyridin-2-yl)benzoate (73 mg, 0.23 mmol) in ethanol (5 mL) and HCl (conc. 1 mL) was added PtO2 (7 mg, 0.023 mmol). The mixture was hydrogenated under a hydrogen atmosphere (35 psi) for 6 h. The reaction mixture was purged with argon, filtered through a 0.2 μm filter, and concentrated. The resulting crude material was taken up with CH2Cl2 (5 mL) after which iPr2NEt (0.1 mL, 0.58 mmol) and acetyl chloride (18 μL, 0.25 mmol) were successively added. The mixture was stirred for 30 min, then diluted with CH2Cl2 (30 mL) and washed successively with 0.5 M HCl (1×10 mL), 9% sodium carbonate (1×10 mL), brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude residue containing the title compound was used without further purification. MS m/z=372 [M+1]+; Calc'd for C23H33NO3: 371.

Workup

  1. customfor 6 h
  2. customThe reaction mixture was purged with argon
  3. filtrationfiltered through a 0.2 μm
  4. filtrationfilter
  5. concentrationconcentrated
  6. additionwere successively added
  7. washwashed successively with 0.5 M HCl (1×10 mL), 9% sodium carbonate (1×10 mL), brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. additionThe crude residue containing the title compound
  12. customwas used without further purification

Sources & evidence

ORD record
ord-1e9e9eee4ea24d09a4ceddc83fbd9b55
Source dataset
uspto-grants-2010_11
Patent number
US07838676B2

Reaction notes

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