Potassium Carbonate → 3-{[3-(dimethylamino)propyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamide

HRID 899911ノート

反応式

HRID 899911 の反応式
F[C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:5]([N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6].[CH2:24]([N:26]([CH2:31]C)[CH2:27][CH2:28][CH2:29][NH2:30])C.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:24][N:26]([CH3:31])[CH2:27][CH2:28][CH2:29][NH:30][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[N+:21]([O-:23])=[O:22])[C:5]([N:7]([CH2:13][CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11])=[O:6]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 61011N,N-Diethyl-1,3-propanediamineHCID 684471113-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide

生成物 1

HCID 687903453-{[3-(dimethylamino)propyl]amino}-N,N-bis(3-methylbutyl)-4-nitrobenzamide収率 68%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 3-fluoro-N,N-bis(3-methylbutyl)-4-nitrobenzamide (2.5 g, 1 eq, prepared according to Example A1), 3-diethylamino-propylamine (877 mg, 1.1 eq) and potassium carbonate (2.13 g, 2 eq) in acetonitrile (80 ml) is heated under reflux for 5 hours then concentrated under reduced pressure at 40° C. The residue is taken up in dichloromethane (130 ml) and water (50 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 by flash chromatography on silica gel (eluent: dichloromethane/methanol 9:1) produces the expected compound in the form of a yellow oil (2.1 g mg; 68% yield).

後処理

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours
  3. concentrationthen concentrated 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 by flash chromatography on silica gel (eluent: dichloromethane/methanol 9:1)

出典と根拠

ORDレコード
ord-92dd63bd94a34bce802ff94e735bac32
出典データセット
uspto-grants-2008_04
特許番号
US07355052B2

反応ノート

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