4-Methylmorpholine → 1-Isopropyl-piperidine-4-carboxaldehyde

HRID 1883071Notes

Reaction equation

HRID 1883071 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][OH:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2].CN1CCOCC1>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH:10]=[O:11])[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 79724-MethylmorpholineHCID 11147855(1-Isopropylpiperidin-4-yl)methanol

Product 1

HCID 178939231-Isopropyl-piperidine-4-carboxaldehydeYield 51.5%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 1-isopropylpiperidine-4-methanol (0.40 g, 2.5 mmol) and N-methylmorpholine (0.46 g, 3.8 mmol) in methylene chloride (20 mL) was treated with tetrapropyl-ammonium perruthenate (0.089 g, 0.25 mmol). After 3 h, the mixture was concentrated and the residue purified by column chromatography (SiO2: 10% to 20% methanol:methylene chloride) affording 0.20 g (50%) of the title compound.

Workup

  1. concentrationthe mixture was concentrated
  2. customthe residue purified by column chromatography (SiO2: 10% to 20% methanol:methylene chloride)

Sources & evidence

ORD record
ord-8a20e59513af49daa75c46d8ac384d53
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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