Water → HCID 71522656, compound

HRID 2178537Notes

Reaction equation

HRID 2178537 reaction equation
C(N(S(F)(F)[F:7])CC)C.O[C:11]([CH3:34])([CH3:33])[CH2:12][CH:13]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]2=[O:32])[CH2:14]1.O>ClCCl>[F:7][C:11]([CH3:34])([CH3:33])[CH2:12][CH:13]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][C:27]2=[O:32])[CH2:14]1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 89500392HCID 89500392, compound

Product 1

HCID 71522656HCID 71522656, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulfur trifluoride (31 μl, 0.235 mmol, 1.5 eq) is added to 1-(2-{2-[3-(2-hydroxy-2-methyl propyl)pyrrolidin-1-yl]ethyl}phenyl)piperidin-2-one a13-2 (54 mg, 0.157 mmol, 1 eq) in dichloromethane (5 ml) dropwise and the reaction mixture stirred at room temperature overnight. The reaction mixture is poured into water and stirring is pursued for 1 hour. After phase separation, the aqueous phase is further extracted with dichloromethane (3 times). The combined organic phases are washed with brine (1 time), dried over Na2SO4, filtered and concentrated under reduced pressure. The residue is purified by basic reverse phase chromatography (gradient: acetonitrile/H2O/ammonium formiate from 5% to 40% of acetonitrile in 8 minutes) to afford 6 mg of 1-(2-{2-[3-(2-fluoro-2-methylpropyl)pyrrolidin-1-yl]ethyl}phenyl)piperidin-2-one 85 as a yellow oil.

Workup

  1. stirringstirring
  2. waitis pursued for 1 hour
  3. customAfter phase separation
  4. extractionthe aqueous phase is further extracted with dichloromethane (3 times)
  5. washThe combined organic phases are washed with brine (1 time)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue is purified by basic reverse phase chromatography (gradient: acetonitrile/H2O/ammonium formiate from 5% to 40% of acetonitrile in 8 minutes)

Sources & evidence

ORD record
ord-b5cbef4b061b456881149744bbae0c52
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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