(Diethylamino)sulfur trifluoride → HCID 18180012, compound

HRID 1359849Notes

Reaction equation

HRID 1359849 reaction equation
CCN(S(F)(F)[F:7])CC.O[CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]#[N:19])[CH2:13][CH2:12]1>C(Cl)Cl>[F:7][CH:11]1[CH2:16][CH2:15][N:14]([CH2:17][C:18]#[N:19])[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 111054492-(4-hydroxypiperidin-1-yl)acetonitrile

Product 1

HCID 18180012HCID 18180012, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DAST (4.36 mL, 33 mmol) was added to a solution of (4-hydroxy-piperidin-1-yl)-acetonitrile (4.25 g, 30 mmol) in DCM (80 mL) at −30° C., the mixture was then stirred at rt for overnight. The reaction was cooled to −30° C. and quenched with methanol (10 mL) for 30 mins. The organic layer was then washed with NaHCO3 and dried. The residue was purified on a silica gel column to give 3 g (71%) of (4-fluoro-piperidin-1-yl)-acetonitrile.

Workup

  1. temperatureThe reaction was cooled to −30° C.
  2. customquenched with methanol (10 mL) for 30 mins
  3. washThe organic layer was then washed with NaHCO3
  4. customdried
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-40242723da6d462587b2a23680811fda
Source dataset
uspto-grants-2003_07
Patent number
US06599902B2

Reaction notes

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