2-Bromopyridine → 3-Methyl-1-pyridin-2-ylpiperazine hydrobromide

HRID 1794211Notes

Reaction equation

HRID 1794211 reaction equation
[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[Br:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1>>[BrH:8].[CH3:1][CH:2]1[NH:3][CH2:4][CH2:5][N:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH2:7]1

Participants

3

Reactant 2

HCID 79732-BromopyridineHCID 660572-Methylpiperazine

Product 1

HCID 118491863-Methyl-1-pyridin-2-ylpiperazine hydrobromideYield 26%

Conditions

Temperature
120 °C

Procedure

2-Methylpiperazine (1.0 g, 0.01 mol, racemic mixture) and 2-bromopyridine (10 mL, 0.1 mol) were combined and heated at 120° C. for 16 hours. The reaction mixture was cooled to 23° C. and partitioned between ethyl acetate and water. The layers were separated, and the water layer was concentrated under reduced pressure. The residue was triturated with ethyl acetate, dichloromethane, and methanol to afford 460 mg (26% yield) of the title compound as an off-white solid. 1H NMR (300 MHz, DMSO-d6) δ 1.27 (d, J=6.6 Hz, 3H), 2.90 (dd, J=10.5, 14.1 Hz, 1H), 3.10 (m, 2H), 3.40 (m, 2H), 4.32 (m, 2H), 6.77 (dd, J=4.8, 6.9 Hz, 1H), 6.98 (d, J=8.1 Hz, 1H), 7.64 (m, 1H), 8.15 (m, 1H), 8.63 (bs, 1H), 8.92 (bs, 1H); MS (APCI) m/e 178 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 23° C.
  2. custompartitioned between ethyl acetate and water
  3. customThe layers were separated
  4. concentrationthe water layer was concentrated under reduced pressure
  5. customThe residue was triturated with ethyl acetate, dichloromethane, and methanol

Sources & evidence

ORD record
ord-2b892320865b4b30a8e2505913aa58ed
Source dataset
uspto-grants-2006_04
Patent number
US07022728B2

Reaction notes

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