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

HRID 1947665Notes

Reaction equation

HRID 1947665 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-ed9f45f80f244c7ab9e91665b99fd544
Source dataset
uspto-grants-2013_03
Patent number
US08399485B2

Reaction notes

Loading…