Methyl formate → 1-Acetylpiperidine

HRID 1112590Notes

Reaction equation

HRID 1112590 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1CCCC1.[CH3:12][O:13]C=O.[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[CH:12]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:13].[C:16]([N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)(=[O:18])[CH3:17]

Participants

6

Reactant 4

HCID 7865Methyl formateHCID 7918Acetic AnhydrideHCID 8082Piperidine2×HCID 31268Pyrrolidine

Product 2

HCID 120581-AcetylpiperidineHCID 174291-Piperidinecarboxaldehyde

Procedure

As starting compound in the process of the invention there is used as 1-acyl-2-alkoxypiperidine or pyrrolidine of the formula II, which is preferably obtained by electrochemical alkoxylation of 1-acyl-piperidine or pyrrolidine. The latter compounds can be obtained, for example, by reacting piperidine or pyrrolidine with an acylating agent, for example an acid chloride, an acid anhydride or an ester; there are mentioned, for example, the reactions of piperidine with a formic acid methyl ester (K. Auwers, Z.f. physik. Chemie, 15, 45 (1894) or acetic anhydride (A. W. Hofmann, Ber.Deut.Chem.Ges., 16, 588 (1883), in which 1-formylpiperidine or 1-acetylpiperidine is obtained in a yield of about 96%.

Sources & evidence

ORD record
ord-a1e49f39c32a494a8a0e9e2a264787d1
Source dataset
uspto-grants-1978_10
Patent number
US04123434

Reaction notes

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