1-Butanol → 1-Acetyl-2-n-butoxypiperidine

HRID 26346

Reaction equation

HRID 26346 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:10]([OH:14])[CH2:11][CH2:12][CH3:13]>F[B-](F)(F)F.C[N+](C)(C)C>[C:1]([N:4]1[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[O:14][CH2:10][CH2:11][CH2:12][CH3:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 2631-ButanolHCID 120581-Acetylpiperidine2×

Product 1

HCID 213228661-Acetyl-2-n-butoxypiperidineYield 57.1%

Reagents, catalysts & solvents 1

HCID 12621Tetramethylammonium tetrafluoroborateCatalyst

Procedure

In the same manner as indicated in Example 6 there are electrolyzed 8.5 g of N-acetylpiperidine and 49.7 g of n-butanol in the presence of 0.3 g of tetramethylammonium tetrafluoroborate as conducting salt. After throughput of 2.5 Faraday per mol of N-acetylpiperidine the current is switched off. The calculated mean cell voltage is 91 volts. Work-up of the electrolysis solution gives 7.6 g of 1-acetyl-2-n-butoxypiperidine (boiling point 70° C./0.1 mbar; nD25 =1.4656), which corresponds to a product yield of 56.8% and a current efficiency of 45.5%.

Sources & evidence

ORD record
ord-9b9a98bbfd09486b8dd6a08cb7fdef27
Source dataset
uspto-grants-1979_04
Patent number
US04149941

Linked notes

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