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

HRID 2403569

반응식

HRID 2403569 반응식
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

참가 물질

5

반응물 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 12010033-Bromo-2-methylpyridineHCID 45051916Sodium tert-butoxide

생성물 1

HCID 68106327Tert-butyl 4-(2-methylpyridin-3-yl)piperazine-1-carboxylate수율 98%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-98cadd563f1c443daa2dfa7faf16755c
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802679B2

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