Hydrochloric Acid → N-[(1R)-1-(4-{[(2S)-2-(4-fluorophenyl)morpholin-4-yl]methyl}phenyl)ethyl]methanesulfonamide hydrochloride

HRID 880243Notes

Reaction equation

HRID 880243 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C@H:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH3:22])=[CH:17][CH:16]=3)[CH2:9]2)=[CH:4][CH:3]=1.[ClH:28]>C(O)(C)C>[ClH:28].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C@H:21]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH3:22])=[CH:17][CH:16]=3)[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71660507N-[(1R)-1-(4-{[(2S)-2-(4-Fluorophenyl)morpholin-4-yl]methyl}phenyl)ethyl]methanesulfonamide

Product 1

HCID 71724619N-[(1R)-1-(4-{[(2S)-2-(4-fluorophenyl)morpholin-4-yl]methyl}phenyl)ethyl]methanesulfonamide hydrochlorideYield 75%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Dissolve N-[(1R)-1-(4-{[(2S)-2-(4-fluorophenyl)morpholin-4-yl]methyl}phenyl)ethyl]methanesulfonamide (50 g, 127.39 mmol) in isopropyl alcohol (200 mL). Add HCl (4M in dioxanes; 63.70 mL, 254.78 mmol) drop-wise to the solution and stir at ambient temperature for 50 min. Remove the volatiles under reduced pressure; add H2O (200 mL); then evaporate the water. Add H2O (200 mL) and isopropyl alcohol (100 mL), and concentrate to a total volume of 80 mL. Filter the resulting thick slurry; wash solid with H2O; collect by filtration; and dry the filter cake under reduced pressure at 55° C. to provide the title compound as a white solid (40.6 g, 75%). MS (m/z): 393 (M-Cl).

Workup

  1. customRemove the volatiles under reduced pressure
  2. customthen evaporate the water
  3. concentrationAdd H2O (200 mL) and isopropyl alcohol (100 mL), and concentrate to a total volume of 80 mL
  4. filtrationFilter the resulting thick slurry
  5. washwash solid with H2O
  6. filtrationcollect by filtration
  7. customand dry the filter cake under reduced pressure at 55° C.

Sources & evidence

ORD record
ord-0bc9eda4bc894ec08a3a93dc362a7528
Source dataset
uspto-grants-2015_03
Patent number
US08993568B2

Reaction notes

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