Dimethylformamide dimethyl acetal → 4-[2-(1-Ethyl-4,5-dihydro-imidazol-2-yl)ethyl]-1-piperidine carboxaldehyde dimethylacetal
Reaction equation
[CH2:1]([N:3]1[CH2:7][CH2:6][N:5]=[C:4]1[CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1)[CH3:2].[CH3:16][O:17][CH:18]([O:22][CH3:23])N(C)C>CO>[CH3:16][O:17][CH:18]([O:22][CH3:23])[N:13]1[CH2:12][CH2:11][CH:10]([CH2:9][CH2:8][C:4]2[N:3]([CH2:1][CH3:2])[CH2:7][CH2:6][N:5]=2)[CH2:15][CH2:14]1Participants
Procedure
A solution of 4-[2-(1-ethyl-4,5-dihydro-imidazol-2-yl)ethyl]piperidine (0.66 g, 0.0031 M) in methanol (6 ml) and dimethylformamide dimethylacetal (6 ml) was heated at 90° C. for 6 hrs. Removal of the excess of dimethylformamide dimethylacetal gave 4-[2-(1-ethyl-4,5-dihydro-imidazol-2-yl)ethyl]-1-piperidine carboxaldehyde dimethylacetal. The solution of the piperidine carboxaldehyde dimethylacetal in chloroform (5 ml) was then added to a mixture of 6-aminopenicillanic acid (0.6 g, 0.0028 M) and diisopropylethylamine (0.5 ml) in chloroform (6 ml) at 0° C. The reaction was stirred at 0° C. for 1 hr and room temperature for 3 hrs. The solvent was removed and water (10 ml) was added. After being washed with ethylacetate, the aqueous solution, acidified from about pH 3 to about 3.5 was purified on Sephadex LH B 20 columns to give [2S-(2-alpha,5alpha, 6beta)]-6-[[[4-[2-(1-ethyl-4,5-dihydro-1H-imidazol-2-yl)ethyl]-1-piperidinyl]methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid hydrochloride (0.46 g, 35% yield).
Workup
- customRemoval of the excess of dimethylformamide dimethylacetal
Sources & evidence
- ORD record
- ord-2251df1895b74f1699f243b3cd48faf8
- Source dataset
- uspto-grants-1984_02
- Patent number
- US04431653
Reaction notes
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