Dimethylformamide dimethyl acetal → 1-(Dimethoxymethyl)-4-(1H-imidazol-2-ylmethyl)piperidine

HRID 364730Notes

Reaction equation

HRID 364730 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][CH:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1.[CH3:13][O:14][CH:15]([O:19][CH3:20])N(C)C>CO>[CH3:13][O:14][CH:15]([O:19][CH3:20])[N:10]1[CH2:11][CH2:12][CH:7]([CH2:6][C:2]2[NH:1][CH:5]=[CH:4][N:3]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 132811984-(1H-Imidazol-2-ylmethyl)piperidine

Product 1

HCID 202397741-(Dimethoxymethyl)-4-(1H-imidazol-2-ylmethyl)piperidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The free base of 4-(1H-imidazol-2-yl-methyl)piperidine (1.0 g, 0.006M) and dimethylformamide dimethylacetal (15 ml) in methanol (20 ml) were heated at 90° C. for 8 hrs. The excess of dimethylformamide dimethylacetal was removed at the reduced pressure to give 4-(1H-imidazol-2-yl-methyl)piperidine carboxaldehyde dimethylacetal. To the mixture of 6-aminopenicillanic acid (1.16 g, 0.0054M) and diisopropyl ethylamine (0.96 ml) in dry chloroform (20 ml) was added the solution (10 ml CHCl3 and 2 ml MeOH) of the above piperidine carboxaldehyde dimethylacetal at 0° C. The reaction was stirred at 0° C. for 1 hr. and then at room temperature for 3 hrs. After this period, the solvent was removed in vacuo and the residue dissolved in water (20 ml). The aqueous solution, washed with ethylacetate was acidified to pH 3 with dilute aqueous HCl and purified on Sephadex LH 20 columns to give [2 S-(2alpha,5alpha,6beta)]-3,3-dimethyl-6-[[[4-(1H-imidazol-2-yl-methyl)-1-piperidinyl]methylene]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid hydrochloride (0.84 g, 33%).

Workup

  1. customThe excess of dimethylformamide dimethylacetal was removed at the reduced pressure

Sources & evidence

ORD record
ord-49a12f8960d7428dbf3c93f77e97a2ee
Source dataset
uspto-grants-1986_08
Patent number
US04605744

Reaction notes

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