Methanol → 1-Benzoyl-2-methyl-6-methoxypiperidine

HRID 1111681

Reaction equation

[C:1]([N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.F[B-](F)(F)F.[CH3:21][OH:22]>>[C:1]([N:9]1[CH:14]([O:22][CH3:21])[CH2:13][CH2:12][CH2:11][CH:10]1[CH3:15])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 887Methanol

HCID 26255Tetrafluoroborate

HCID 275047N-Benzoyl-2-methylpiperidine2×

Product 1

HCID 213228541-Benzoyl-2-methyl-6-methoxypiperidineYield 77.6%

Procedure

In the same manner as in Example 5, there are electrolyzed 43.8 g of 1-benzoyl-2-methylpiperidine and 60.2 g of methanol in the presence of 0.3 of tertramethylammonium tetrafluoroborate as conducting salt. After throughput of 2.5 Faraday per mol of 1-benzoyl-2-methylpiperidine the current is switched off. After work-up of the electrolysis solution, 39.0 g of 1-benzoyl-2-methyl-6-methoxypiperidine (boiling point 78°-81° C./0.1 mm Hg; nD25 = 1.5340) are obtained which corresponds to a product yield of 77.5% and a current efficiency of 62.0%.

Sources & evidence

ORD record: ord-b5c92a24f5e7493f82a339da950a4ae1
Source dataset: uspto-grants-1978_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04118500

Linked notes

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