Methanol → 1-Acetyl-2-methoxyhexahydroazepine

HRID 26347

Reaction equation

HRID 26347 reaction equation
[C:1]([N:4]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH3:11][OH:12]>F[B-](F)(F)F.C[N+](C)(C)C>[C:1]([N:4]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH:5]1[O:12][CH3:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 220591-(Azepan-1-yl)ethan-1-one2×

Product 1

HCID 147617821-Acetyl-2-methoxyhexahydroazepineYield 90.3%

Reagents, catalysts & solvents 1

HCID 12621Tetramethylammonium tetrafluoroborateCatalyst

Procedure

In the same manner as indicated in Example 6 there are electrolyzed 23.2 g of N-acetylhexahydroazepine and 57.7 g of methanol in the presence of 0.26 g of tetramethylammonium tetrafluoroborate as conducting salt. After throughput of 2.5 Faraday per mol of N-acetylhexahydroazepine the current is switched off. The calculated mean cell voltage is 40.8 volts. Work-up of the electrolysis solution gives 25.4 g of 1-acetyl-2-methoxyhexahydroazepine (boiling point 53° C./0.06 mbar; nD25 =1.4775), which corresponds to a product yield of 90.1% and a current efficiency of 71.5%.

Sources & evidence

ORD record
ord-f1bbe5f957834a998990a825faeda54f
Source dataset
uspto-grants-1979_04
Patent number
US04149941

Linked notes

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