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

HRID 1684343

반응식

HRID 1684343 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2f3893689a25493d8ac0e22bf5aac241
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639913

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