tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate

HRID 2403569

Reaction equation

Br[C:2]1[C:3]([CH3:8])=[N:4][CH:5]=[CH:6][CH:7]=1.[N:9]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.[Na].CC(O)(C)C>C1(C)C=CC=CC=1>[CH3:8][C:3]1[C:2]([N:12]2[CH2:11][CH2:10][N:9]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:14][CH2:13]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

Conditions

Temperature: 100 °C

Procedure

3-Bromo-2-methylpyridine (500 mg) and tert-butyl piperazine-1-carboxylate (650 mg) were dissolved in toluene (7.5 ml), and (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one_palladium (3:2) (40 mg), 1,1′-binaphthalene-2,2′-diylbis(diphenylphosphine) (18 mg), and 2-methylpropan-2-ol sodium (391 mg) were added thereto in this order under a nitrogen atmosphere, followed by warming to 100° C. and stirring overnight. The reaction mixture was subjected to liquid separation with CHCl3 and water, the organic layer was dried over Na2SO4, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (CHCl3 to 5% MeOH/CHCl3) to obtain tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate (790 mg) as a pale yellow oil.

Workup

customThe reaction mixture was subjected to liquid separation with CHCl3 and water
dry with materialthe organic layer was dried over Na2SO4
customthe solvent was evaporated
customThe obtained residue was purified by silica gel column chromatography (CHCl3 to 5% MeOH/CHCl3)

Sources & evidence

ORD record: ord-98cadd563f1c443daa2dfa7faf16755c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08802679B2

Linked notes

Loading…