Pyrazine, 2-chloro-3-methyl- → HCID 86755576, compound

HRID 1870227Notes

Reaction equation

HRID 1870227 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][OH:11])[C@H:6]([OH:12])[CH2:5]1.Cl[C:14]1[C:19]([CH3:20])=[N:18][CH:17]=[CH:16][N:15]=1.[O-2].[Ca+2]>C(Cl)Cl.CO>[CH3:20][C:19]1[C:14]([NH:1][CH2:2][CH2:3][N:4]2[CH2:9][CH2:8][C@H:7]([CH2:10][OH:11])[C@H:6]([OH:12])[CH2:5]2)=[N:15][CH:16]=[CH:17][N:18]=1

Participants

5

Reactant 3

HCID 66769Pyrazine, 2-chloro-3-methyl-HCID 6850728CalciumoxideHCID 86755577HCID 86755577, compound

Product 1

HCID 86755576HCID 86755576, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of (±)-cis-1-(2-aminoethyl)-3-hydroxy-4-piperidinemethanol (0.064 mol), 2-chloro-3-methylpyrazine (0.068 mol) and calcium oxide (0.145 mol) was stirred for 5 hours at 120° C. The reaction mixture was cooled. The mixture was dissolved in CH2Cl2 /CH3OH and filtered over dicalite. The filtrate was evaporated and the residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 90/10). The desired fractions were collected and the solvent was evaporated. The oily residue was triturated in CH3CN. The precipitate was filtered off and dried, yielding 4 g (23.5%) of (±)-cis-1-[2-[(3-methyl-2-pyrazinyl)amino]ethyl]-3-hydroxy-4-piperidinemethanol (interm. 5a).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered over dicalite
  3. customThe filtrate was evaporated
  4. customthe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 90/10)
  5. customThe desired fractions were collected
  6. customthe solvent was evaporated
  7. customThe oily residue was triturated in CH3CN
  8. filtrationThe precipitate was filtered off
  9. customdried

Sources & evidence

ORD record
ord-e35d0c48cf2e4cf79efd406f0177c1b3
Source dataset
uspto-grants-2000_08
Patent number
US06096761

Reaction notes

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