Dimethylformamide dimethyl acetal → 4-(1H-imidazol-2-yl)-1-piperidine carboxaldehyde dimethylacetal
Reaction equation
C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.[NH:15]1[CH:19]=[CH:18][N:17]=[C:16]1[CH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C[O-].[Na+].[CH3:29][O:30][CH:31]([O:35][CH3:36])N(C)C>CO>[CH3:29][O:30][CH:31]([O:35][CH3:36])[N:23]1[CH2:24][CH2:25][CH:20]([C:16]2[NH:15][CH:19]=[CH:18][N:17]=2)[CH2:21][CH2:22]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of the dihydrochloride salt of 4-(1H-imidazol-2-yl)piperidine (0.448 g, 0.002M) in methanol (15 ml) which contained sodium methoxide (0.004M) was stirred at room temperature for about 5 minutes and dimethylformamide dimethyl acetal (10 ml) was added and the mixture was heated at 80° C. for 8 hrs. The excess of dimethylformamide dimethylacetal was removed to give 4-(1H-imidazol-2-yl)-1-piperidine carboxaldehyde dimethylacetal. This acetal was then dissolved in 6 ml of chloroform. To a mixture of 6-aminopenicillanic acid (0.388 g, 0.0018M) and diisopropylethylamine (0.2 ml) in CHCl3 (20 ml) was added the chloroform solution of the above piperidine carboxaldehyde dimethylacetal at 0° C. The reaction was stirred at 0° C. for 1 hr and room temperature for 3 hrs. After this period, the solvent was removed and the residue dissolved in water (15 ml). The aqueous solution, washed with ethylacetate, was acidified to pH 3 with dil. HCl and purified on Sephadex LH 20 to give [2S-(2alpha,5alpha,6beta)]-6-[[[4-(1H-imidazol-2-yl)-1-piperidinyl)methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid hydrochloride trihydrate (0.245 g, 26% yield).
Workup
- temperaturethe mixture was heated at 80° C. for 8 hrs
- customThe excess of dimethylformamide dimethylacetal was removed
Sources & evidence
- ORD record
- ord-b0e4d33921ee4230aafbc74e35c4d43a
- Source dataset
- uspto-grants-1985_08
- Patent number
- US04537969
Reaction notes
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