Hydrochloric Acid → Ethyl 3-methoxy-4-((1-methylpiperidin-4-yl)methoxy)benzoate
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22](OC(C)(C)C)=O)[CH2:18][CH2:17]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7].C=O.Cl.CCOCC>C(O)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[CH:12][C:13]=1[O:14][CH2:15][CH:16]1[CH2:17][CH2:18][N:19]([CH3:22])[CH2:20][CH2:21]1)[C:6]([O:8][CH2:9][CH3:10])=[O:7]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 95 °C
Procedure
To a solution of ethyl 3-methoxy-4-(1-tert-butyloxycarbonylpiperidin-4-ylmethoxy)benzoate (35 g, 89 mmol) in formic acid (35 ml) was added formaldehyde (12M, 37% in water, 35 ml, 420 mmol). After stirring at 95° C. for 3 hours, the volatiles were removed by evaporation. The residue was dissolved in methylene chloride and 3M hydrogen chloride in ether (40 ml, 120 mmol) was added. After dilution with ether, the mixture was triturated until a solid was formed. The solid was collected by filtration, washed with ether and dried under vacuum overnight at 50° C. to give ethyl 3-methoxy-4-(1-methylpiperidin-4-ylmethoxy)benzoate (30.6 g, quant.).
Workup
- customthe volatiles were removed by evaporation
- dissolutionThe residue was dissolved in methylene chloride
- customAfter dilution with ether, the mixture was triturated until a solid
- customwas formed
- filtrationThe solid was collected by filtration
- washwashed with ether
- customdried under vacuum overnight at 50° C.
Sources & evidence
- ORD record
- ord-8f4614e3d4ec43c8b70f2a4b840526b2
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492560B2
Reaction notes
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