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Chlorosuccinimide → Tert-butyl 1'-(5-chloropyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

HRID 2093465
Notes
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Reaction equation

HRID 2093465 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.[Cl:26]N1C(=O)CCC1=O>CN(C=O)C.[Cl-].[Na+].O>[Cl: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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 31398ChlorosuccinimideHCID 54581959Tert-butyl 1'-pyrazin-2-yl-4,4'-bipiperidine-1-carboxylate

Product 1

HCID 59178890Tert-butyl 1'-(5-chloropyrazin-2-yl)-4,4'-bipiperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

The tert-butyl 1′-pyrazin-2-yl-4,4′-bipiperidine-1-carboxylate (64 mg, 0.19 mmol, prepared as described for Example 8) and N-chlorosuccinimide (27 mg, 0.20 mmol) were dissolved in DMF (0.9 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 10% 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 10% acetone

Sources & evidence

ORD record
ord-aefc1897617245439222c862a948d26a
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08445499B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes