Triethylamine → N-(2-n-Propylpentanoyl)-1-aminoindan

HRID 1604476ノート

反応式

HRID 1604476 の反応式
[C:1](Cl)(=[O:9])[CH:2]([CH2:6][CH2:7][CH3:8])[CH2:3][CH2:4][CH3:5].[NH2:11][CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1.CCN(CC)CC.CCOC(C)=O>C1(C)C=CC=CC=1.O>[CH2:3]([CH:2]([CH2:6][CH2:7][CH3:8])[C:1]([NH:11][CH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1)=[O:9])[CH2:4][CH3:5]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 762402-Propylvaleryl chlorideHCID 123445(+-)-1-Aminoindan

生成物 1

HCID 11658951N-(2-n-Propylpentanoyl)-1-aminoindan収率 69.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of valproyl chloride (1.55 g, 9.6 mmole) in toluene (25 ml) was added dropwise to a stirred and ice-cooled solution of 1-aminoindan (1.47 g, 10.0 mmole) and Et3N (1.11 g, 11 mmole) . The mixture was stirred at ambient temperature for 17 hours, EtOAc (60 ml) and water (50 ml) were added and the phases were separated. The organic phase was washed successively with 0.1N HCl (40 ml), 0.1N NaHCO3 (40 ml) and saturated NaCl (40 ml), dried over magnesium sulphate and evaporated to dryness under reduced pressure. The residue was treated with hexane (15 ml, 30 min stirring, RT) and filtered. The crude product was crystallized from hexane:EtOAc (70:30 mixture), to give 1.72 g (6.65 mmole, 69%) of a white crystalline solid, mpt: 133-4° C.

後処理

  1. stirringThe mixture was stirred at ambient temperature for 17 hours
  2. customthe phases were separated
  3. washThe organic phase was washed successively with 0.1N HCl (40 ml), 0.1N NaHCO3 (40 ml) and saturated NaCl (40 ml)
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness under reduced pressure
  6. additionThe residue was treated with hexane (15 ml, 30 min stirring, RT)
  7. filtrationfiltered
  8. customThe crude product was crystallized from hexane:EtOAc (70:30 mixture)

出典と根拠

ORDレコード
ord-c6771f5025c142c88c55c3054a02397a
出典データセット
uspto-grants-1999_11
特許番号
US05994408

反応ノート

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