Thionyl Chloride → HCID 22707864, compound

HRID 1261656Notes

Reaction equation

HRID 1261656 reaction equation
O[C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])[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:23][C:21]([F:22])([F:24])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 49760255tert-Butyl 4-hydroxy-4-[2-(trifluoromethyl)phenyl]piperidine-1-carboxylate

Product 1

HCID 22707864HCID 22707864, compoundYield 29,021.699%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of tert-butyl 4-hydroxy-4-[2-(trifluoromethyl)phenyl]piperidine-1-carboxylate (0.75 g, 2.2 mmol) in pyridine (15 mL) cooled in an ice bath was slowly added thionyl chloride (0.79 mL, 11 mmol) and the mixture was warmed to room temperature and stirred overnight (17 h). The reaction was quenched with ice water. The resulting solution was extracted with methylene chloride three times. The combined extracts were dried (MgSO4), filtered, and concentrated. Purification by flash chromatography on silica gel (0-40% B over 25 min. Bottle A=hexanes, Bottle B=EtOAc) gave 209 g of the desired product as a solid. MS calculated for C17H20F3NO2: (M+H) 328; found 228.0 (M-Boc+H).

Workup

  1. customThe reaction was quenched with ice water
  2. extractionThe resulting solution was extracted 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 (0-40% B over 25 min

Sources & evidence

ORD record
ord-7b5b3ba60a914276a062581660563812
Source dataset
uspto-grants-2013_06
Patent number
US08470827B2

Reaction notes

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