Guaiacol → HCID 66851807, compound

HRID 517007Notes

Reaction equation

HRID 517007 reaction equation
Cl[CH2:2][C:3]([N:5]1[C@H:10]([CH3:11])[CH2:9][N:8]([S:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)(=[O:14])=[O:13])[CH2:7][C@@H:6]1[CH3:25])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH3:32][O:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[OH:40]>C(#N)C.O>[CH3:25][C@H:6]1[CH2:7][N:8]([S:12]([C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)(=[O:13])=[O:14])[CH2:9][C@@H:10]([CH3:11])[N:5]1[C:3](=[O:4])[CH2:2][O:40][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[O:33][CH3:32]

Participants

6

Reactant 3

HCID 460GuaiacolHCID 11430Potassium CarbonateHCID 67980526HCID 67980526, compound

Product 1

HCID 66851807HCID 66851807, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-Chloro-1-((2S,6R)-2,6-dimethyl-4-(naphthalene-2-ylsulfonyl)piperazin-1-yl)ethanone (200 mg, 0.52 moles) was dissolved in 20 mL of acetonitrile. Dry K2CO3 (106 mg, 0.79 moles) was added to the reaction mixture under nitrogen atmosphere and allowed to stir for about ten minutes. 2-methoxyphenol (97 mg, 0.78 moles) was slowly added to the reaction at room temperature and allowed the reaction to continue for another 4 h. The reaction was monitored by TLC and after product formation was observed, the reaction mixture was diluted with cold water (10 mL) and extracted with ethyl acetate (25 mL×2). The combined organic layers were washed with bicarbonate followed by brine & then dried over sodium sulphate. The solvent was evaporated on reduced pressure to afford crude product which was purified by column chromatography to yield the title compound as an off-white solid.

Workup

  1. customthe reaction
  2. extractionextracted with ethyl acetate (25 mL×2)
  3. washThe combined organic layers were washed with bicarbonate
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was evaporated on reduced pressure
  6. customto afford crude product which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-ca8e7fb953054407a126097ca6e5e29d
Source dataset
uspto-grants-2015_08
Patent number
US09115086B2

Reaction notes

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