Thionyl Chloride → 1,1-Dimethylethyl 4-(chloromethyl)-3,6-dihydro-1(2H)-pyridinecarboxylate

HRID 266905Notes

Reaction equation

HRID 266905 reaction equation
[CH3:1][C:2]([CH3:15])([O:4][C:5]([N:7]1[CH2:12][CH2:11][C:10](=[CH2:13])[CH:9](O)[CH2:8]1)=[O:6])[CH3:3].S(Cl)([Cl:18])=O.C([O-])(O)=O.[Na+]>C1C=CC=CC=1>[CH3:1][C:2]([CH3:15])([O:4][C:5]([N:7]1[CH2:12][CH2:11][C:10]([CH2:13][Cl:18])=[CH:9][CH2:8]1)=[O:6])[CH3:3]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 10584700tert-Butyl 3-hydroxy-4-methylidenepiperidine-1-carboxylate

Product 1

HCID 109988611,1-Dimethylethyl 4-(chloromethyl)-3,6-dihydro-1(2H)-pyridinecarboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
60 °C

Procedure

The intermediate obtained from Step A (400 mg, 1.88 mmole) was dissolved in 10 mL benzene and thionyl chloride (165 ml, 2.26 mmole) was added and heated to 60° C. for 25 minutes. The resulting mixture was poured into NaHCO3 (aq.) and extracted with ether. The ether layer was dried over magnesium sulfate and concentrated to give title compound (333 mg, 77%).

Workup

  1. extractionextracted with ether
  2. dry with materialThe ether layer was dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-27bbf3bb86a34c0689399efaebf72fa3
Source dataset
uspto-grants-1997_07
Patent number
US05652235

Reaction notes

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