Formic Acid → 6-(4-Isopropylpiperazin-1-yl)picolinaldehyde

HRID 1519446Notes

Reaction equation

HRID 1519446 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[N:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]2)[CH:9]=[CH:8][CH:7]=1.C(O)=O>O>[CH:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]2[N:11]=[C:6]([CH:2]=[O:1])[CH:7]=[CH:8][CH:9]=2)[CH2:17][CH2:16]1)([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 284Formic AcidHCID 867193571-[6-(1,3-Dioxolan-2-yl)pyridin-2-yl]-4-isopropylpiperazine

Product 1

HCID 867193586-(4-Isopropylpiperazin-1-yl)picolinaldehydeYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 1-[6-(1,3-dioxolan-2-yl)pyridin-2-yl]-4-isopropylpiperazine (8, 0.31 g, 1.1 mmol), formic acid (2.50 g, 50 mmol) and water (0.5 mL) was heated at 60° C. for 5 h. After this time, the mixture was concentrated and the residue was purified by silica gel chromatography eluting with 0-10% methanol in dichloromethane to afford the title compound (0.21 g, 82%) as a yellow oil; ESI MS m/z 234 [M+H]+.

Workup

  1. concentrationAfter this time, the mixture was concentrated
  2. customthe residue was purified by silica gel chromatography
  3. washeluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-11de8dd6cbba4b299637463dfc964014
Source dataset
uspto-grants-2015_07
Patent number
US09073878B2

Reaction notes

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