Hydrochloric Acid → 4-[(Azetidin-3-yloxy)methyl]pyridine dihydrochloride

HRID 2172024Notes

Reaction equation

HRID 2172024 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][CH:9]2[CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10]2)=[CH:3][CH:2]=1.[ClH:20]>C(OCC)C>[ClH:20].[ClH:20].[NH:11]1[CH2:12][CH:9]([O:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67154567Tert-butyl 3-(pyridin-4-ylmethoxy)azetidine-1-carboxylate

Product 1

HCID 671547314-[(Azetidin-3-yloxy)methyl]pyridine dihydrochlorideYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of tert-butyl 3-(pyridin-4-ylmethoxy)azetidine-1-carboxylate (313 mg, 1.18 mmol; which may be prepared as described in Step 3) in diethyl ether (4 mL) at 0° C. was added HCl 2N in diethyl ether (12 mL). The reaction mixture was stirred for 1 h then mixture was filtered. The resulting solid was rinsed with diethyl ether and collected to give the title compound as a white solid (155 mg, 65%).

Workup

  1. filtrationmixture was filtered
  2. washThe resulting solid was rinsed with diethyl ether
  3. customcollected

Sources & evidence

ORD record
ord-b5907afe5d1c4004910252a581a91590
Source dataset
uspto-grants-2015_06
Patent number
US09051321B2

Reaction notes

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