1-Methylpiperazine → 1-(3-Chloro-5-fluoropyridin-4-yl)-4-methylpiperazine

HRID 524876Notes

Reaction equation

HRID 524876 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1I.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.CCN(C(C)C)C(C)C>CC#N>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([F:9])[C:7]=1[N:14]1[CH2:15][CH2:16][N:11]([CH3:10])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 81531DiisopropylethylamineHCID 110325453-Chloro-5-fluoro-4-iodopyridine

Product 1

HCID 867209331-(3-Chloro-5-fluoropyridin-4-yl)-4-methylpiperazine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-chloro-5-fluoro-4-iodo-pyridine (2.18 g, 8.468 mmol), 1-methylpiperazine (1.272 g, 1.409 mL, 12.70 mmol) and DIPEA (2.189 g, 2.950 mL, 16.94 mmol) in MeCN (13.08 mL) was heated at 130° C. in the microwave for 300 min. The reaction mixture was concentrated in vacuo and purified by column chromatography on silica eluting with 0-10% MeOH/DCM. Product fractions were combined and concentrated in vacuo to leave 1-(3-chloro-5-fluoropyridin-4-yl)-4-methylpiperazine as a yellow/brown oil. (1.16 g, 59%). MS (ES+) 230.0.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompurified by column chromatography on silica eluting with 0-10% MeOH/DCM
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-519e7f74b0924db494484f010e6ab549
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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