Hydrochloric Acid → 5.6-Dichloro-3-(2-(S)-azetidinylmethoxy)pyridine hydrochloride

HRID 617373Notes

Reaction equation

HRID 617373 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@@H:11]2[CH2:14][CH2:13][NH:12]2)[CH:5]=[N:6][C:7]=1[Cl:8].Cl>CCOCC>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([O:9][CH2:10][C@@H:11]2[CH2:14][CH2:13][NH:12]2)[CH:5]=[N:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 102633765,6-Dichloro-3-(2-(S)-azetidinylmethoxy)pyridine

Product 1

HCID 213097065.6-Dichloro-3-(2-(S)-azetidinylmethoxy)pyridine hydrochlorideYield 162.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The compound from step 109c (338 mg, 1.45 mmol) was slurried in ether (15 mL), and ether saturated with HCl gas was added. Solvent was removed and the remaining white solid was recrystallized from methanol/Et2O to give 317 mg of short white needles, 81% yield. m.p.=181-182° C. MS (CI) m/e 233 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 8.13 (d, J=2.9 Hz, 1H), 7.79 (d, J=2.9 Hz, 1H), 4.99-4.91 (m, 1H), 4.44 (d, J=4.4 Hz, 2H), 4.21-4.03 (m, 2H), 2.74-2.65 (m, 2H). Anal. calc. for C9H11Cl3N2O: C, 40.10; H, 4.11; N, 10.39; Found: C, 39.89; H, 4.08; N, 10.25.

Workup

  1. customSolvent was removed
  2. customthe remaining white solid was recrystallized from methanol/Et2O

Sources & evidence

ORD record
ord-51da3c924fd8487abc51a4d5c4ea9c28
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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