Hydrochloric Acid → Methyl 3-(1,2,3,6-tetrahydropyridin-4-yl)benzoate

HRID 643572Notes

Reaction equation

S(Cl)(Cl)=O.Cl.C(OC([N:13]1[CH2:18][CH:17]=[C:16]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([OH:24])=[O:23])[CH2:15][CH2:14]1)=O)(C)(C)C.[CH3:28]O>>[NH:13]1[CH2:18][CH:17]=[C:16]([C:19]2[CH:20]=[C:21]([CH:25]=[CH:26][CH:27]=2)[C:22]([O:24][CH3:28])=[O:23])[CH2:15][CH2:14]1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 592610253-(1-(Tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzoic acid

Product 1

HCID 59261054Methyl 3-(1,2,3,6-tetrahydropyridin-4-yl)benzoate

Procedure

Thionyl chloride (2.39 mL, 32.7 mmol) was added dropwise to 15 mL of anhydrous methanol. The resulting anhydrous methanolic HCl solution was added to 3-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzoic acid (3.31 g, 10.9 mmol) and the reaction mixture was stirred at rt for 6 h. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (silica, 5-10% stepwise gradient in 1% increments of 10% NH4OH (28% solution)/methanol in DCM) to give methyl 3-(1,2,3,6-tetrahydropyridin-4-yl)benzoate. ESI-MS calc. for C13H15NO2: 217; Found: 218 (M+H).

Workup

customThe solvent was removed under reduced pressure
customthe residue was purified by flash chromatography (silica, 5-10% stepwise gradient in 1% increments of 10% NH4OH (28% solution)/methanol in DCM)

Sources & evidence

ORD record: ord-9908f8da5a764723ba01dc37c5ced410
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700591B2

Reaction notes

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