Piperidine → HCID 68453506, compound

HRID 2357573Notes

Reaction equation

HRID 2357573 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](Cl)=[N:7][N:6]=[CH:5]2.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([N:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[N:7][N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 8082PiperidineHCID 11430Potassium CarbonateHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 68453506HCID 68453506, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of 6-bromo-1-chlorophthalazine (Example 1, 0.1 g, 0.41 mmol), piperidine (0.081 mL, 0.82 mmol) and potassium carbonate (0.056 g, 0.41 mmol) in 5 mL acetonitrile was added to a glass microwave reaction vessel. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 180° C. for 20 min. After about 20 min., all starting material was converted to product (M+1=292, 294). The mixture was concentrated under vacuum and purified via flash chromatography (silica gel) eluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM to give (0.13 g) 6-bromo-1-(piperidin-1-yl)phthalazine as yellow solid. Found MS (ES+): 292, 294(M+H)+.

Workup

  1. additionwas added to a glass microwave reaction vessel
  2. concentrationThe mixture was concentrated under vacuum
  3. custompurified via flash chromatography (silica gel)
  4. washeluting with a gradient of 2% 2 M ammonia in MeOH/DCM to 6% 2 M ammonia in MeOH/DCM

Sources & evidence

ORD record
ord-a7ad35ad4fab489aa8ceaaf685c791ef
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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