Propanal → Propanal

HRID 1447507Notes

Reaction equation

HRID 1447507 reaction equation
[CH:1](=[O:4])[CH2:2][CH3:3].[NH:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.O=O.CN(C1C=CC2N=C3C(=CC(C=C3)=[N+](C)C)SC=2C=1)C>C(Cl)Cl>[CH:1]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[CH:1](=[O:4])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 527PropanalHCID 977OxygenHCID 4139Methylene blue cationHCID 8083Morpholine

Product 2

HCID 527PropanalHCID 20417N-Formylmorpholine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Mixture of propionaldehyde (VII, 2.73 mmole) and morpholine (5.76 mmole) in methylene chloride was irradiated for 90 min with oxygen bubbling in the presence of methylene blue. N-formylmorpholine was obtained in 103% yield on the basis of (VII), as expected. Further, mixture of propionaldehyde (2.73 mmole) and morpholine (11.52 mmole) gave N-formylmorpholine in 145% yield. When n-octylaldehyde (VIII) was used, the yield of N-formylmorpholine went up to 272% by irradiation for 240 min. (Table III.) Also the reaction of mixture of (VIII) and piperidine affords the same results. For example, N-formylpiperidine was obtained in 282% yield for 1.29 mmole of (VIII) and 20.5 mmole of (V). Also, N-formylpiperidine was obtained in 281% yield for the mole ratio of piperidine (V) to n-octylaldehyde (VIII) being 9 for 280 min.

Sources & evidence

ORD record
ord-6cd1e9dbfd0946e4a7e83ef48f641e32
Source dataset
uspto-grants-1979_12
Patent number
US04177121

Reaction notes

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