Hydrochloric Acid → Ethyl 3-methoxy-4-((1-methylpiperidin-4-yl)methoxy)benzoate

HRID 2233253Notes

Reaction equation

C=O.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH:18]1[CH2:23][CH2:22][N:21]([C:24](OC(C)(C)C)=O)[CH2:20][CH2:19]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9].Cl.C(OCC)C>O.C(O)=O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH:18]1[CH2:19][CH2:20][N:21]([CH3:24])[CH2:22][CH2:23]1)[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

Conditions

Temperature: 95 °C

Procedure

Formaldehyde (35 ml of a 37% solution in water, 420 mmol) was added to a solution of ethyl 3-methoxy-4-(1-tert-butyloxycarbonylpiperidin-4-ylmethoxy)benzoate (35 g, 89 mmol) in formic acid (35 ml) and the reaction was heated at 95° C. for 3 hours. The reaction was cooled, the volatiles we re removed in vacuo and the residue was dissolved in dichloromethane. 3.0N Hydrogen chloride in diethyl ether (40 ml, 120 mmol) was added, together with a little diethyl ether and a solid was precipitated. Collection of the solid by suction filtration followed by drying in vacuo yielded ethyl 3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)benzoate (30.6 g, 100% yield) as a white solid:

Workup

temperatureThe reaction was cooled
customthe volatiles we re removed in vacuo
dissolutionthe residue was dissolved in dichloromethane
customa solid was precipitated
customCollection of the solid
filtrationby suction filtration
customby drying in vacuo

Sources & evidence

ORD record: ord-5913f3c0222a43d5afb23bb1c9eceaa9
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709479B1

Reaction notes

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