Potassium Carbonate → 4-(6-Formylpyridin-2-yl)-N-isopropylpiperazine-1-carboxamide

HRID 922406Notes

Reaction equation

HRID 922406 reaction equation
C(=O)(OC)O[C:3]1[CH:8]=[CH:7][C:6]([O:9]C)=[CH:5][CH:4]=1.[CH:14]([NH:17][C:18]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)=[O:19])([CH3:16])[CH3:15].C([O-])([O-])=O.[K+].[K+].C[N:33](C)C(=O)C>>[CH:6]([C:7]1[N:33]=[C:5]([N:23]2[CH2:24][CH2:25][N:20]([C:18]([NH:17][CH:14]([CH3:16])[CH3:15])=[O:19])[CH2:21][CH2:22]2)[CH:4]=[CH:3][CH:8]=1)=[O:9]

Participants

5

Reactant 4

HCID 11430Potassium CarbonateHCID 31374DimethylacetamideHCID 5797864-Methoxyphenyl methyl carbonateHCID 16740267N-Isopropylpiperazine-1-carboxamide

Product 1

HCID 867193624-(6-Formylpyridin-2-yl)-N-isopropylpiperazine-1-carboxamideYield 24%

Conditions

Temperature
80 °C

Procedure

A mixture of 6-bromopicolinaldehyde (5, 1.00 g, 5.38 mmol) and N-isopropylpiperazine-1-carboxamide (4, 1.10 g, 6.45 mmol) in N,N-dimethylacetamide (20 mL) was treated with K2CO3 (2.23 g, 16.1 mmol) and heated at 80° C. for 18 h. The mixture was cooled to room temperature and concentrated. The residue was purified by silica gel chromatography eluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH to afford the title compound (0.35 g, 24%) as an impure yellow solid: Multimode MS m/z 172 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was purified by silica gel chromatography
  4. washeluting with hexanes to 100% EtOAc to 4:1 EtOAc/MeOH

Sources & evidence

ORD record
ord-eb1a2e2a0c304c08a236161817f76348
Source dataset
uspto-grants-2016_03
Patent number
US09278940B2

Reaction notes

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