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

HRID 1767729Notes

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 removed in vacuo and the residue was dissolved in dichloromethane. 3.0 N 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 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-b51fef20406d493abec03084bf35be17
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235559B1

Reaction notes

Loading…