HCID 71212260, compound → (4-Methoxy-3-methylphenyl)-4-piperidinylmethanone

HRID 1752237Notes

Reaction equation

HRID 1752237 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][N:12](C(=O)C)[CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[CH3:20]>Cl.C(OCC)C>[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[CH3:20]

Participants

4

Reactant 1

HCID 71212260HCID 71212260, compound

Product 1

HCID 20613914(4-Methoxy-3-methylphenyl)-4-piperidinylmethanone

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

A suspension of 1-(4-(4-methoxy-3-methylbenzoyl)piperidin-1-yl)ethanone (5.45 g, 19.8 mmol) in 6 N HCl (40 mL) was heated to reflux for 12 h then concentrated in vacuo to a light purple solid. The material was taken up in ˜100 mL MeOH with heating and sonication, concentrated in vacuo to ˜25 mL, added diethyl ether (˜200 mL) to form white precipitate and a purple aqueous layer. The aqueous layer was removed via a pipet and concentrated in vacuo. The suspension was decanted through filter to recover a white solid (1.30 g). The aqueous material was concentrated in vacuo to form a purplish oil which was taken up in diethyl ether and the resulting suspension was filtered (0.82 g). The filtrate was concentrated in vacuo to a purple oil. The solid material was confirmed to be the title compound. Calculated molecular formula=C14H19NO2=233.31. found MS (ESI) m/e 233.9 (M+H+)

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 12 h
  3. concentrationthen concentrated in vacuo to a light purple solid
  4. temperaturewith heating
  5. customsonication
  6. concentrationconcentrated in vacuo to ˜25 mL
  7. additionadded diethyl ether (˜200 mL)
  8. customto form white precipitate
  9. customThe aqueous layer was removed via a pipet
  10. concentrationconcentrated in vacuo
  11. customThe suspension was decanted
  12. filtrationthrough filter
  13. customto recover a white solid (1.30 g)
  14. concentrationThe aqueous material was concentrated in vacuo
  15. customto form a purplish oil which
  16. filtrationthe resulting suspension was filtered (0.82 g)
  17. concentrationThe filtrate was concentrated in vacuo to a purple oil

Sources & evidence

ORD record
ord-ada828c924f34f35ba097c66d5e0ccc1
Source dataset
uspto-grants-2015_10
Patent number
US09163003B2

Reaction notes

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