Triethylamine → 4-[2-(Inden-1-yl)ethyl]-1-(4-aminocarbonylphenyl)piperazine

HRID 1417833노트

반응식

HRID 1417833 반응식
[CH:1]1([CH2:10][CH2:11]O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CN(C1C=CC=CN=1)C.C(N(CC)CC)C.CS(Cl)(=O)=O.[N:34]1([C:40]2[CH:45]=[CH:44][C:43]([C:46]([NH2:48])=[O:47])=[CH:42][CH:41]=2)[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(N(C(C)C)CC)(C)C>O1CCCC1.O.C(O)CO>[CH:1]1([CH2:10][CH2:11][N:37]2[CH2:36][CH2:35][N:34]([C:40]3[CH:41]=[CH:42][C:43]([C:46]([NH2:48])=[O:47])=[CH:44][CH:45]=3)[CH2:39][CH2:38]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

10

반응물 6

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 111065094-(1-Piperazinyl)benzamideHCID 232887512-(1H-Inden-1-yl)ethan-1-ol

생성물 1

HCID 232887964-[2-(Inden-1-yl)ethyl]-1-(4-aminocarbonylphenyl)piperazine

시약·촉매·용매 3

HCID 174Ethylene Glycol용매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 2-(inden-1-yl)ethanol (CXVI-B, EXAMPLE 86, 0.8 g, 5 mmol), dimethylaminopyridine (0.02 g, 0.2 mmol) and triethylamine (1.7 ml, 12.5 mmol) in tetrahydrofuran (10 ml) is cooled to 0° and methanesulfonyl chloride (0.43 ml, 5.5 mmol) is added dropwise. After 45 min, 4-(piperazinyl)benzenecarboxamide (LXV, 1.23 g, 6 mmol), diisopropylethylamine (1.0 ml, 6 mmol) and ethyleneglycol (10 ml) are added and heated at 85° for 60 hr. The mixture is diluted with water and extracted with methylene chloride. The organic phase is separated, washed with saline, dried (magnesium sulfate), filtered and concentrated. Crystallization from ethyl acetate gives the title compound, mp 207°; NMR (CDCl3, TMS) 7.75-6.90, 6.28 and 3.39-2.68 δ.

후처리

  1. temperatureis cooled to 0°
  2. temperatureheated at 85° for 60 hr
  3. extractionextracted with methylene chloride
  4. customThe organic phase is separated
  5. washwashed with saline
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customCrystallization from ethyl acetate

출처 및 근거

ORD 기록
ord-6dcce1f5c79041e1bea1eab68d316846
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877317

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