Thionyl Chloride → HCID 66370955, compound

HRID 1770796Notes

Reaction equation

HRID 1770796 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[C:14]([CH2:15]O)=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:2]2.O=S(Cl)[Cl:19]>ClCCl>[Cl:19][CH2:15][C:14]1[C:9]([N:3]2[CH2:4][CH:5]3[O:8][CH:1]([CH2:7][CH2:6]3)[CH2:2]2)=[N:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 66369774(2-(8-Oxa-3-azabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)methanol

Product 1

HCID 66370955HCID 66370955, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cooled (0° C.) solution of (2-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)pyridin-3-yl)methanol (0.070 g, 0.32 mmol) in dichloromethane was added SOCl2 (0.23 mL, 3.2 mmol) and the reaction mixture was allowed to warm to ambient temperature. After 1 h, the reaction mixture was concentrated and azeotroped with toluene three times to provide 3-(3-(chloromethyl)pyridin-2-yl)-8-oxa-3-azabicyclo[3.2.1]octane (0.075 g, 98%) as a clear oil. MS (ES) for C12H15ClN2O: 239 (MH+).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customazeotroped with toluene three times

Sources & evidence

ORD record
ord-03ff698d611e425894f70cdaf931af13
Source dataset
uspto-grants-2016_02
Patent number
US09248199B2

Reaction notes

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