rel-(2R,6S)-2,6-dimethylpiperazine → HCID 178461499, compound

HRID 2206335Notes

Reaction equation

HRID 2206335 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[N:3]=1.[CH3:11][C@H:12]1[CH2:17][NH:16][CH2:15][C@@H:14]([CH3:18])[NH:13]1>CS(C)=O>[CH3:11][C@H:12]1[NH:13][C@@H:14]([CH3:18])[CH2:15][N:16]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:10])[N:3]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 6950261rel-(2R,6S)-2,6-dimethylpiperazineHCID 178519593HCID 178519593, compound

Product 1

HCID 178461499HCID 178461499, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

6-Chloro-2-hydroxynicotinaldehyde (1.06 g, 6.76 mmol) was dissolved in DMSO (20 mL) at room temperature. The solution was treated with cis-2,6-dimethylpiperazine (1.16 g, 10.18 mmol) at room temperature. The reaction mixture was stirred at 100° C. for 3 hours and cooled to room temperature to yield crude 6-(cis-3,5-dimethylpiperazin-1-yl)-2-hydroxynicotinaldehyde. MS m/z 236 [M+H]+.

Workup

  1. temperaturecooled to room temperature

Sources & evidence

ORD record
ord-4316fbdb8b17406393611c7d145f0ef0
Source dataset
uspto-grants-2016_06
Patent number
US09371336B2

Reaction notes

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