HCID 86686019, compound → 1440520-38-6

HRID 2277725Notes

Reaction equation

HRID 2277725 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:17]2[CH:22]=[N:21][CH:20]=[C:19]([Cl:23])[N:18]=2)(C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CC1C=CC=CC=1C.CC(N(C)C)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:17]2[CH:22]=[N:21][CH:20]=[C:19]([Cl:23])[N:18]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86686019HCID 86686019, compound

Product 1

HCID 534152801440520-38-6Yield 44.9%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 31374DimethylacetamideSolvent

Procedure

A solution of 3-(6-chloro-pyrazin-2-yl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester (46 g) in o-xylene (300 mL) and DMA (30 mL) was heated under reflux for 5 hrs. After cooling to room temperature, it was washed with brine (200 mL×2). The organic layer was then dried over anhy. Na2SO4, filtered, and concentrated in vacuo. The residue obtained was then purified on a silica gel column eluting with EA:DCM:Hex=1:1:3 to give the title compound (18 g) as a white solid. MS: 298.7 (M+H+).

Workup

  1. temperatureunder reflux for 5 hrs
  2. washit was washed with brine (200 mL×2)
  3. customThe organic layer was then dried over anhy
  4. filtrationNa2SO4, filtered
  5. concentrationconcentrated in vacuo
  6. customThe residue obtained
  7. customwas then purified on a silica gel column
  8. washeluting with EA

Sources & evidence

ORD record
ord-3c018f19e2ed4e9885291d1b18d0916f
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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