Methyl triflate → HCID 57840752, compound

HRID 1476671Notes

Reaction equation

HRID 1476671 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]2[C:17](=[O:18])[CH2:16][CH2:15]N(C)[CH2:13]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2].CO[S:22](C(F)(F)F)(=O)=O.O.S.[Na].O.O.O.O.O.O.O.O.O.[S-2].[Na+].[Na+]>CC(C)CC(=O)C.O.CC(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:12]2[C:17](=[O:18])[CH2:16][CH2:15][S:22][CH2:13]2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH3:2]

Participants

8

Reactant 4

HCID 9526Methyl triflateHCID 73972Sodium sulfide nonahydrateHCID 53442613Sodium hydrogen sulfide hydrateHCID 53855653HCID 53855653, compound

Product 1

HCID 57840752HCID 57840752, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
2 °C

Procedure

To a suspension of 3-(3-ethoxy-4-methoxy-phenyl)-1-methyl-piperidin-4-one (0.88 g) in 8.5 ml of 4-methyl-pentan-2-one, which is cooled to about 2° C., trifluoro-methansulfonic acid methylester (0.6 g) is added dropwise within about 9 min. Following 20 min stirring at RT a combined solution of sodium hydrogensulfide monohydrate (0.82 g) and sodium sulfide nonahydrate (0.98 g) in 8.5 ml of water is added and the stirred reaction mixture is then heated to reflux temperature for 4 h. Cooled to RT the stirring is stopped and the building up organic layer is separated. The water phase is washed three times with 2 ml each of EtOAc. The collected organic phase is washed two times with 3 ml each of water, filtered and concentrated in vacuo giving a solid residue. This is suspended in 2-propanol (4 ml) and the suspension is heated to reflux temperature giving a clear solution. The continuously stirred solution is slowly cooled down to RT inducing a spontaneous crystallization. Following stirring for 15 h at RT, the suspension is further stirred at about 2° C. for 2 h and then the crystals are filtered of, washed with 2-propanol (1 ml) and dried in vacuo at about 60° C. for 24 h yielding the title compound.

Workup

  1. additionis added
  2. customthe stirred reaction mixture
  3. temperatureis then heated
  4. temperatureto reflux temperature for 4 h
  5. temperatureCooled to RT the stirring
  6. customthe building up organic layer is separated
  7. washThe water phase is washed three times with 2 ml each of EtOAc
  8. washThe collected organic phase is washed two times with 3 ml each of water
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customgiving a solid residue
  12. temperaturethe suspension is heated
  13. temperatureto reflux temperature
  14. customgiving a clear solution
  15. temperatureThe continuously stirred solution is slowly cooled down to RT
  16. customa spontaneous crystallization
  17. stirringthe suspension is further stirred at about 2° C. for 2 h
  18. filtrationthe crystals are filtered of,
  19. washwashed with 2-propanol (1 ml)
  20. customdried in vacuo at about 60° C. for 24 h

Sources & evidence

ORD record
ord-73a7e0c3ef974415b9969081ec756805
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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