Hydrochloric Acid → 2-Methyl-3-(4-{4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl}phenoxy)propane-1,2-diol

HRID 1909094Notes

Reaction equation

HRID 1909094 reaction equation
[F:1][C:2]([F:34])([F:33])[O:3][C:4]1[CH:32]=[CH:31][C:7]([O:8][CH:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][C:23]4([CH3:30])[CH2:27][O:26]C(C)(C)[O:24]4)=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[CH:6][CH:5]=1.C(O)C.Cl.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.O>[CH3:30][C:23]([OH:24])([CH2:22][O:21][C:18]1[CH:19]=[CH:20][C:15]([N:12]2[CH2:11][CH2:10][CH:9]([O:8][C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:34])([F:1])[F:33])=[CH:32][CH:31]=3)[CH2:14][CH2:13]2)=[CH:16][CH:17]=1)[CH2:27][OH:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 10340Sodium CarbonateHCID 673611244-[4-(Trifluoromethoxy)phenoxy]-1-{4-[(2,2,4-trimethyl-1,3-dioxolan-4-yl)methoxy]phenyl}piperidine

Product 1

HCID 533455662-Methyl-3-(4-{4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl}phenoxy)propane-1,2-diolYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-[4-(Trifluoromethoxy)phenoxy]-1-{4-[(2,2,4-trimethyl-1,3-dioxolan-4-yl)methoxy]phenyl}piperidine (223 mg, 0.463 mmol), ethanol (10 mL), and concentrated hydrochloric acid (2 mL) were mixed and stirred at room temperature for 14 hours. Water was added to the reaction mixture, followed by neutralization with sodium carbonate. Ethyl acetate was added to the mixture to conduct extraction. The organic layer was washed with water three times. The organic layer was concentrated under reduced pressure, obtaining 196 mg (yield: 96%) of the objective compound.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with water three times
  3. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9b754cd50a224bc8a3e3151308539ff2
Source dataset
uspto-grants-2013_12
Patent number
US08598358B2

Reaction notes

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