Thionyl Chloride → HCID 59833546, compound

HRID 1436788Notes

Reaction equation

HRID 1436788 reaction equation
O[C:2]1([C:15]2[CH:16]=[N:17][CH:18]=[C:19]([C:21]([F:24])([F:23])[F:22])[CH:20]=2)[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.S(Cl)(Cl)=O>N1C=CC=CC=1>[F:24][C:21]([F:22])([F:23])[C:19]1[CH:20]=[C:15]([C:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:4][CH:3]=2)[CH:16]=[N:17][CH:18]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59833545HCID 59833545, compound

Product 1

HCID 59833546HCID 59833546, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-4-[5-(trifluoromethyl)pyridin-3-yl]piperidine-1-carboylate (300 mg, 0.433 mmol) in pyridine (3.00 mL) cooled in an ice bath was added thionyl chloride (0.158 mL, 2.16 mmol). After being stirred at room temperature overnight (16 h), the brown reaction mixture was quenched with ice water and extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (0 - 20% B over 35 min. Bottle A =hexanes, Bottle B =EtOAc) provided 65 mg (46%) of desired product as a light yellow oil. LC-MS calculated for C16H19F3N2O2:(M+H) 329; found 329.1.

Workup

  1. customthe brown reaction mixture was quenched with ice water
  2. extractionextracted with methylene chloride three times
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography on silica gel (0 - 20% B over 35 min

Sources & evidence

ORD record
ord-feceb826f2764222bfedb83cf48fbc2f
Source dataset
uspto-grants-2009_11
Patent number
US07618970B2

Reaction notes

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