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

HRID 490179Notes

Reaction equation

HRID 490179 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%

Procedure

A solution of 2-methylpiperazine (1.0 g, 0.01 mol, racemic mixture) and 2-bromopyridine (10 mL, 0.1 mol) was heated to 120° C. for 16 hours. The reaction mixture was cooled to room temperature 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 racemic 3-methyl-1-pyridin-2-yl-piperazine hydrobromide 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 (br s, 1H), 8.92 (br s, 1H); MS (APCI) m/e 178 (M+H) +.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe layers were separated
  3. concentrationthe water layer was concentrated under reduced pressure
  4. customThe residue was triturated with ethyl acetate, dichloromethane, and methanol

Sources & evidence

ORD record
ord-fbe66b8f7de24771a21325786cd7aabf
Source dataset
uspto-grants-2009_05
Patent number
US07528134B2

Reaction notes

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