Thionyl Chloride → HCID 90417175, compound

HRID 1484814Notes

Reaction equation

HRID 1484814 reaction equation
O[CH2:2][C:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:11])[CH3:10])[CH2:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O=S(Cl)[Cl:20]>C(Cl)Cl>[Cl:20][CH2:2][C:3]1[CH2:8][CH2:7][N:6]([C:9](=[O:11])[CH3:10])[CH2:5][C:4]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 90409015HCID 90409015, compound

Product 1

HCID 90417175HCID 90417175, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(hydroxymethyl)-3-phenyl-5,6-dihydropyridin-1(2H)-yl)ethanone (86 mg, 0.37 mmol) in DCM (2 mL) was added SOCl2 (0.67 mL, 9.25 mmol). After stirred at RT for 15 min, the mixture was concentrated and was diluted with Sat. NaHCO3 and EtOAc, organic layer was separated and the aqueous layer was extracted with EtOAc, organic layer ere combined, washed with brine, dried and concentrated to give crude oil, which was purified by column (Hexanes/EtOAc=100:0 to 25:75) to give 1-(4-(chloromethyl)-5-phenyl-3,6-dihydropyridin-1(2H)-yl)ethan-1-one (35 mg).

Workup

  1. concentrationthe mixture was concentrated
  2. additionwas diluted with Sat. NaHCO3 and EtOAc, organic layer
  3. customwas separated
  4. extractionthe aqueous layer was extracted with EtOAc, organic layer ere
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated
  8. customto give crude oil, which
  9. customwas purified by column (Hexanes/EtOAc=100:0 to 25:75)

Sources & evidence

ORD record
ord-a46aacd8fb854ddf8f21b155cf100bbe
Source dataset
uspto-grants-2016_08
Patent number
US09422279B2

Reaction notes

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