(5-Hydroxymethyl-pyridin-2-yl)-(4-isopropyl-piperazin-1-yl)-methanone → 6-(4-Isopropyl-piperazine-1-carbonyl)-pyridine-3-carbaldehyde

HRID 30456Notes

Reaction equation

HRID 30456 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH:17]([CH3:19])[CH3:18])[CH2:13][CH2:12]2)=[O:10])=[N:7][CH:8]=1>C(Cl)Cl.O=[Mn]=O>[CH:17]([N:14]1[CH2:13][CH2:12][N:11]([C:9]([C:6]2[N:7]=[CH:8][C:3]([CH:2]=[O:1])=[CH:4][CH:5]=2)=[O:10])[CH2:16][CH2:15]1)([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 44515775(5-Hydroxymethyl-pyridin-2-yl)-(4-isopropyl-piperazin-1-yl)-methanone

Product 1

HCID 445157766-(4-Isopropyl-piperazine-1-carbonyl)-pyridine-3-carbaldehydeYield 95%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-hydroxymethyl-pyridin-2-yl)-(4-isopropyl-piperazin-1-yl)-methanone (0.275 g, 1.10 mmol) in DCM (30 mL) was added MnO2 (0.400 g., 5.20 mmol). The reaction was stirred for 6 h, filtered through a pad of diatomaceous earth, and concentrated to give the desired aldehyde (0.250 g, 95%).

Workup

  1. filtrationfiltered through a pad of diatomaceous earth
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a5651e1e91dc45858ccd3e7b0dad7c23
Source dataset
uspto-grants-2008_09
Patent number
US07423147B2

Reaction notes

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