Potassium Carbonate → 1-(6-bromo-1-phthalazinyl)-3-Piperidinecarboxamide

HRID 2357579Notes

Reaction equation

[NH:1]1[CH2:9][CH2:8][CH2:7][CH:3]([C:4]([NH2:6])=[O:5])[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][CH2:7][CH:3]([C:4]([NH2:6])=[O:5])[CH2:2]1)=[N:16][N:15]=[CH:14]2

Participants

Conditions

Temperature: 190 °C

Procedure

A glass microwave reaction vessel was charged with nipecotamide (0.17 g, 1.4 mmol), 6-bromo-1-chlorophthalazine (0.110 g, 0.45 mmol), potassium carbonate (0.062g, 0.45 mmol) and 3 mL acetonitrile. The reaction mixture was stirred and heated in a Smith Synthesizer® microwave reactor (Personal Chemistry, Inc., Upssala, Sweden) at 190° C. for 20 min (watts, Powermax feature on, ramp time 1 min). The mixture was purified directly via flash chromatography (silica gel) eluting with 4/1 hexanes/EtOAc to 4/1 hexanes/EtOAc to give (0.15 g) 1-(6-bromophthalazin-1-yl)piperidine-3-carboxamide as a white solid. Found MS (ES+): 335, 337(M+H)+.

Workup

customA glass microwave reaction vessel
customThe mixture was purified directly via flash chromatography (silica gel)
washeluting with 4/1 hexanes/EtOAc to 4/1 hexanes/EtOAc

Sources & evidence

ORD record: ord-eb1dfb960eaf4de5a78fb5a73849f933
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07759337B2

Reaction notes

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