N-bromobutanimide → Tert-butyl 1'-(5-bromopyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

HRID 2093466Notes

Reaction equation

HRID 2093466 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[N:7]1[CH2:12][CH2:11][CH:10]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]2)[CH2:9][CH2:8]1.[Br:26]N1C(=O)CCC1=O>CN(C=O)C.[Cl-].[Na+].O>[Br:26][C:5]1[N:4]=[CH:3][C:2]([N:7]2[CH2:12][CH2:11][CH:10]([CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH2:9][CH2:8]2)=[N:1][CH:6]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 54581959Tert-butyl 1'-pyrazin-2-yl-4,4'-bipiperidine-1-carboxylate

Product 1

HCID 59178948Tert-butyl 1'-(5-bromopyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

The tert-butyl 1′-pyrazin-2-yl-4,4′-bipiperidine-1-carboxylate (16 mg, 0.046 mmol, prepared as described for Example 8) and N-bromosuccinimide (8.2 mg, 0.046 mmol) were dissolved in DMF (0.2 ml) and the solution stirred overnight at 50 C. The slurry was diluted with 15% brine:water (40 ml) and extracted with ethyl acetate (3×25 ml). The combined organic fraction was washed with brine, dried over magnesium sulfate, filtered, and the volatiles removed in vac. The crude material was purified by chromatography on silica gel with 20% acetone:hexanes to yield the title compound.

Workup

  1. extractionwater (40 ml) and extracted with ethyl acetate (3×25 ml)
  2. washThe combined organic fraction was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe volatiles removed in vac
  6. customThe crude material was purified by chromatography on silica gel with 20% acetone

Sources & evidence

ORD record
ord-a9b17a5298cc4bb3ae23c18e5b2970f5
Source dataset
uspto-grants-2013_05
Patent number
US08445499B2

Reaction notes

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