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Dibutylamine → N6,N6-dibutyl-3-nitro-N2-(3-piperidin-1-ylpropyl)pyridine-2,6-diamine

HRID 1727036
ノート
印刷プレビュー

反応式

HRID 1727036 の反応式
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([NH:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH2:8][CH2:9][CH3:10].Cl[C:17]1[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:20]([N+:33]([O-:35])=[O:34])=[CH:19][CH:18]=1>C(#N)C>[CH2:7]([N:11]([CH2:12][CH2:13][CH2:14][CH3:15])[C:17]1[N:22]=[C:21]([NH:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)[C:20]([N+:33]([O-:35])=[O:34])=[CH:19][CH:18]=1)[CH2:8][CH2:9][CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8148DibutylamineHCID 11430Potassium CarbonateHCID 860008436-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine

生成物 1

HCID 86000846N6,N6-dibutyl-3-nitro-N2-(3-piperidin-1-ylpropyl)pyridine-2,6-diamine収率 95%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

実験手順

Potassium carbonate (54 mg, 2 eq) and a solution of dibutylamine (30 mg, 1.2 eq) in acetonitrile (2 ml) are added successively to a solution of 6-chloro-3-nitro-N-(3-piperidin-1-ylpropyl)pyridin-2-amine (59 mg, 1 eq) in acetonitrile (3 ml). The mixture is heated to reflux for 15 hours then cooled down to ambient temperature and concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (200 ml) and water (90 ml). After decantation and extractions, the combined organic phases are washed with salt water, dried over Na2SO4 then concentrated under reduced pressure at 40° C. Purification of the residue obtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1 to 100% ethyl acetate), produces the expected compound (73 mg; 95% yield).

後処理

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 15 hours
  3. concentrationconcentrated under reduced pressure at 40° C
  4. extractionAfter decantation and extractions
  5. washthe combined organic phases are washed with salt water
  6. dry with materialdried over Na2SO4
  7. concentrationthen concentrated under reduced pressure at 40° C
  8. customPurification of the residue
  9. customobtained, by flash chromatography on silica gel (eluent: heptane/ethyl acetate 1:1 to 100% ethyl acetate)

出典と根拠

ORDレコード
ord-d1a2709a203244a1a1d59758a017f006
出典データセット
uspto-grants-2009_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07495009B2

反応ノート

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