Potassium Carbonate → 4-Tert-butoxycarbonylamino-4-methyl-1-(2-pyrazinyl)piperidine

HRID 456745Notes

Reaction equation

[CH3:1][C:2]1([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:23]1[CH:28]=[N:27][CH:26]=[CH:25][N:24]=1>CN(C)C=O>[CH3:1][C:2]1([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:4][N:5]([C:23]2[CH:28]=[N:27][CH:26]=[CH:25][N:24]=2)[CH2:6][CH2:7]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of tert-butyl (4-methyl-4-piperidinyl)carbamate obtained in Example 10–5 (415 mg) and potassium carbonate (321 mg) in N,N-dimethylformamide (4.5 mL), was added chloropyrazine (665 mg). The mixture was heated at 100° C. with stirring for 24 hrs. The resulting mixture was partitioned between saturated aqueous sodium hydrogencarbonate and ethyl acetate. The organic layer was washed with water and brine, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane and ethyl acetate (2:1) to give the title compound as a pale yellow oil (566 mg).

Workup

customThe resulting mixture was partitioned between saturated aqueous sodium hydrogencarbonate and ethyl acetate
washThe organic layer was washed with water and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel eluting with hexane and ethyl acetate (2:1)

Sources & evidence

ORD record: ord-a4ec64e3892a4549b69f216d8a858ab8
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07186731B2

Reaction notes

Loading…