5-Bromo-2-nitropyridine → 4-Methyl-1-(6-nitropyridin-3-yl)piperidin-4-ol

HRID 1431191Notes

Reaction equation

HRID 1431191 reaction equation
[CH3:1][C:2]1([OH:8])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.Br[C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[N:14][CH:15]=1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O.CCOC(C)=O>[CH3:1][C:2]1([OH:8])[CH2:7][CH2:6][N:5]([C:10]2[CH:15]=[N:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[CH2:4][CH2:3]1

Participants

6

Reactant 2

HCID 8176205-Bromo-2-nitropyridineHCID 156491744-Methylpiperidin-4-ol

Product 1

HCID 667433724-Methyl-1-(6-nitropyridin-3-yl)piperidin-4-olYield 68.2%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Methylpiperidin-4-ol (2.72 g, 23.6 mmol), 5-bromo-2-nitropyridine (3.2 g, 15.8 mmol), and tetrabutylammonium iodide (72 mg, 195 umol) in DMSO (20 ml) was heated to 120° C. for 18 hr. After cooling to room temperature, the reaction mixture was then diluted with EtOAc and washed with water (3×20 mL). The organic phase was then concentrated and triturated with ether to give 4-methyl-1-(6-nitropyridin-3-yl)piperidin-4-ol as a yellow solid (2.55 g, 68.2%). (M+H)+=327.9 m/e.

Workup

  1. washwashed with water (3×20 mL)
  2. concentrationThe organic phase was then concentrated
  3. customtriturated with ether

Sources & evidence

ORD record
ord-42a56a1a172545919982d3299c5b2c41
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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