4-Piperidinecarboxamide → HCID 68453488, compound

HRID 2357578Notes

Reaction equation

HRID 2357578 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17](Cl)=[N:16][N:15]=[CH:14]2.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Br:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[C:17]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1)=[N:16][N:15]=[CH:14]2

Participants

5

Reactant 3

HCID 37724-PiperidinecarboxamideHCID 11430Potassium CarbonateHCID 220304246-Bromo-1-chlorophthalazine

Product 1

HCID 68453488HCID 68453488, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of the isonipecotamide (71 mg, 554 μmol), 6-bromo-1-chlorophthalazine (Example 1, 90 mg, 370 μmol) and potassium carbonate (51 mg, 370 μmol) in 5 mL acetonitrile was added to a glass microwave reaction vessel. The reaction mixture was stirred and heated in a Smith Synthesizes microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 190° C. for about 20 min. at which the starting material was consumed, by TLC, to form product (M+1=335, 337). The mixture was concentrated and purified by column, eluting with a gradient of 2% 2M ammonia in MeOH/DCM to 10% 2M ammonia in MeOH/DCM to give 1-(6-bromophthalazin-1-yl)piperidine-4-carboxamide (0.115g) as a pale yellow solid. Found MS (ES+): 335, 337(M+H)+.

Workup

  1. additionwas added to a glass microwave reaction vessel
  2. temperatureheated in a Smith
  3. customSynthesizes microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 190° C. for about 20 min. at which the starting material
  4. customwas consumed, by TLC
  5. customto form product (M+1=335, 337)
  6. concentrationThe mixture was concentrated
  7. custompurified by column
  8. washeluting with a gradient of 2% 2M ammonia in MeOH/DCM to 10% 2M ammonia in MeOH/DCM

Sources & evidence

ORD record
ord-ac120d0c021f4a90aead0c422a009fda
Source dataset
uspto-grants-2010_07
Patent number
US07759337B2

Reaction notes

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