Pyrrolidine → HCID 20550699, compound
Reaction equation
N1CCCC1.N1(CC(=C)C(=[O:16])C)CCCCC1.[N:18]1([CH2:24][CH:25]([CH2:29][N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)[C:26]([CH3:28])=[O:27])[CH2:23][CH2:22]C[CH2:20][CH2:19]1>>[CH2:19]([N:18]([CH2:24][CH:25]([CH2:29][N:30]1[CH2:35][CH2:34][CH:33]([OH:16])[CH2:32][CH2:31]1)[C:26](=[O:27])[CH3:28])[CH2:23][CH3:22])[CH3:20]Participants
Procedure
The intermediate olefinic ketone is prepared by the procedure of H. M. E. Carwell [J. Chem. Soc., 1058 (1950)]. The ketone obtained from A., 22.8 g., in 25 ml. of ethanol was added to a solution of 25 g. of anhydrous oxalic acid in 75 ml. of ethanol. The mixture was cooled to 0° C., filtered to remove diethylamine hydrogen oxalate and the mother liquor evaporated to dryness under reduced pressure. The residue was dissolved in a little water, treated with potassium carbonate and extracted with ether. The ether was dried over anhydrous sodium sulphate and the residue obtained by solvent removal was distilled. After re-distillation the product was obtained as an oil, b.p. 82° C./18 mm. Similarly, the other 1,1-bis-(disubstituted aminomethyl)acetones obtained as in A. can be converted to the corresponding 3-disubstituted aminomethylbut-3-en-2-ones. The disubstituted amino term as previously indicated also comprises pyrrolidine and piperidine alicyclic ring analogs. For example, 3-(piperidinomethyl)but-3-en-2-one boils at 135°-139° C./15 mm. and is synthesized following the same procedure from 1,1-bis(-piperidinomethyl)acetone.
Workup
- customand is synthesized
Sources & evidence
- ORD record
- ord-342695cc6f7445dda3c804ac6ee7cb86
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04250184
Reaction notes
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