Pyrazine, 2-chloro-3-methyl- → 1-[2-[(3-Methyl-2-pyrazinyl)amino]-ethyl]4-piperidinemethanol

HRID 392062Notes

Reaction equation

HRID 392062 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][OH:11])[CH2:6][CH2:5]1.Cl[C:13]1[C:18]([CH3:19])=[N:17][CH:16]=[CH:15][N:14]=1>>[CH3:19][C:18]1[C:13]([NH:1][CH2:2][CH2:3][N:4]2[CH2:5][CH2:6][CH:7]([CH2:10][OH:11])[CH2:8][CH2:9]2)=[N:14][CH:15]=[CH:16][N:17]=1

Participants

3

Reactant 2

HCID 66769Pyrazine, 2-chloro-3-methyl-HCID 19104142[1-(2-Aminoethyl)piperidin-4-yl]methanol

Product 1

HCID 109339381-[2-[(3-Methyl-2-pyrazinyl)amino]-ethyl]4-piperidinemethanolYield 29%

Conditions

Temperature
120 °C

Procedure

A mixture of 1-(2-amino-ethyl)-4-piperidinemethanol (5.2 g), 2-chloro-3-methyl-pyrazine (5.0 g) and CaO (4.5 g) was stirred for 20 hours at 120° C. The reaction mixture was cooled and purified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 92/8). The pure fractions were collected and the solvent was evaporated, yielding 2.3 g (29%) 1-[2-[(3-methyl-2-pyrazinyl)amino]-ethyl]4-piperidinemethanol (intermediate 1).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompurified by column chromatography over silica gel (eluent: CH2Cl2/(CH3OH/NH3) 92/8)
  3. customThe pure fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-95aee6ebb4c74eada13a147ef5fdef2b
Source dataset
uspto-grants-2004_10
Patent number
US06800628B2

Reaction notes

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