Diisopropylethylamine → tert-Butyl 4-(4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)piperazine-1-carboxylate

HRID 1295559노트

반응식

HRID 1295559 반응식
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][CH2:9][N:8]([S:12]([CH3:15])(=[O:14])=[O:13])[C:7]=2[CH:16]=1.[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(CC)C(C)C)(C)C>CC(O)C>[CH3:15][S:12]([N:8]1[C:7]2[CH:16]=[C:3]([CH2:2][N:20]3[CH2:19][CH2:18][N:17]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21]3)[CH:4]=[CH:5][C:6]=2[O:11][CH2:10][CH2:9]1)(=[O:14])=[O:13]

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 694200776-Bromomethyl-4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine

생성물 1

HCID 86597571tert-Butyl 4-(4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl)piperazine-1-carboxylate수율 71.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

6-Bromomethyl-4-methanesulfonyl-3,4-dihydro-2H-benzo[1,4]oxazine (2.6 g, 8.5 mmol) and tert-butyl piperazine-1-carboxylate (1.58 g, 8.5 mmol) were treated with propan-2-ol (100 mL) followed by N,N-diisopropylethylamine (10.96 g, 85 mmol) and the resulting mixture heated at reflux for 72 h then evaporated to dryness under reduced pressure. The residue was partitioned between ethyl acetate and saturated NaHCO3 aq. and the phases separated. The organic phase was washed with water, saturated brine, dried (MgSO4) and evaporated to dryness under reduced pressure. Chromatography on SiO2, eluting with ethyl acetate in 60°–80° petroleum ether, gave the title compound (2.5 g, 71%) as a brown foam.

후처리

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 72 h
  3. customthen evaporated to dryness under reduced pressure
  4. customThe residue was partitioned between ethyl acetate and saturated NaHCO3 aq.
  5. customthe phases separated
  6. washThe organic phase was washed with water, saturated brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness under reduced pressure
  9. washChromatography on SiO2, eluting with ethyl acetate in 60°–80° petroleum ether

출처 및 근거

ORD 기록
ord-2859919803cd427ea887c1b1fcc014f3
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244726B2

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