Morpholine → 4-(5-Morpholino-3-nitropyridin-2-yl)morpholine

HRID 1431379ノート

反応式

HRID 1431379 の反応式
Cl[C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C1(P(C2CCCCC2)C2(C(C)C)CC(C(C)C)=CC(C(C)C)=C2C2C=CC=CC=2)CCCCC1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[O:11]1[CH2:12][CH2:13][N:8]([C:5]2[N:6]=[CH:7][C:2]([N:17]3[CH2:22][CH2:21][O:20][CH2:19][CH2:18]3)=[CH:3][C:4]=2[N+:14]([O-:16])=[O:15])[CH2:9][CH2:10]1

参加物

7

反応物 4

HCID 8083MorpholineHCID 23676156Sodium t-butoxideHCID 596312064-(5-Chloro-3-nitropyridin-2-yl)morpholineHCID 672859322-Dicyclohexylphosphino-2,4,6-triisopropylbiphenyl

生成物 1

HCID 596312774-(5-Morpholino-3-nitropyridin-2-yl)morpholine

試薬・触媒・溶媒 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium触媒HCID 1140Toluene溶媒

実験手順

To a stirred solution of 4-(5-chloro-3-nitropyridin-2-yl)morpholine (2.48 g, 10 mmol; described herein) in toluene (190 mL) were sequentially added morpholine (1.8 mL, 20 mmol), tris(dibenzylideneacetone)dipalladium(o) (0.65 g, 0.71 mmol), 2-(dicyclohexylphosphino)-2,4,6,-tri-i-propyl-1,1-biphenyl (0.73 g, 1.5 mmol), and sodium tert-butoxide (2.0 g, 20 mmol). The reaction was heated to reflux overnight, cooled to rt, and concentrated. The resulting residue was taken up in EtOAc, washed with satd aq. sodium bicarbonate solution and brine, and the organic layer dried (magnesium sulfate) and concentrated. Column chromatography afforded 4-(6-morpholino-5-nitropyridin-3-yl)morpholine as a red oil. Mass Spectrum (ESI) m/e=295.1 (M+1).

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. washwashed with satd aq. sodium bicarbonate solution and brine
  5. dry with materialthe organic layer dried (magnesium sulfate)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-131aa12eec73447c943a8e72586d910e
出典データセット
uspto-grants-2015_01
特許番号
US08940724B2

反応ノート

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