Benzenebutanamine → (4-Phenyl-butyl)-(2-trifluoromethyl-7,8-dihydro-3H-6,9-dioxa-1,3-diaza-cyclopenta[a]naphthalen-8-ylmethyl)-amine

HRID 392677노트

반응식

HRID 392677 반응식
CC1C=CC(S(O[CH2:12][C@@H:13]2[O:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]4[NH:25][C:24]([C:26]([F:29])([F:28])[F:27])=[N:23][C:20]4=3)[O:15][CH2:14]2)(=O)=O)=CC=1.[C:30]1([CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CS(C)=O.C(OCC)(=O)C>[C:30]1([CH2:36][CH2:37][CH2:38][CH2:39][NH:40][CH2:12][CH:13]2[O:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]4[NH:25][C:24]([C:26]([F:28])([F:29])[F:27])=[N:23][C:20]4=3)[O:15][CH2:14]2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

참가 물질

5

반응물 2

HCID 83242BenzenebutanamineHCID 12071004[(8R)-2-trifluoromethyl-7,8-dihydro-3H-6,9-dioxa-1,3-diaza-cyclopenta[a]naphthalen-8-yl]methyl 4-methylbenzenesulfonate

생성물 1

HCID 9931109(4-Phenyl-butyl)-(2-trifluoromethyl-7,8-dihydro-3H-6,9-dioxa-1,3-diaza-cyclopenta[a]naphthalen-8-ylmethyl)-amine수율 49.3%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매

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온도
85 °C

실험 절차

A mixture of 0.50 g (1.2 mmole) of [(8R)-2-trifluoromethyl-7,8-dihydro-3H-6,9-dioxa-1,3-diaza-cyclopenta[a]naphthalen-8-yl]methyl 4-methylbenzenesulfonate and 0.75 g (5.0 mmole) of 4-phenylbutylamine in 25.0 mL of DMSO was heated at 80-90° C. under nitrogen for 4 hours. The reaction was allowed to come to room temperature, diluted to 500 mL with ethyl acetate, washed with 500 mL portions of saturated aqueous sodium bicarbonate and water, dried over sodium sulfate, filtered and evaporated in vacuum. The residue was column chromatographed on silica gel with 2% methanol in chloroform as eluant and the product fractions evaporated to give 0.24 g of the desired product. This was recrystallized from ethanol with the addition of oxalic acid to give 0.092 g of the (S)-enantiomer of the title compound as a white solid oxalate, hydrate, m.p. 124-127° C.

후처리

  1. customto come to room temperature
  2. washwashed with 500 mL portions of saturated aqueous sodium bicarbonate and water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuum
  6. customchromatographed on silica gel with 2% methanol in chloroform as eluant
  7. customthe product fractions evaporated

출처 및 근거

ORD 기록
ord-ba16abdbd6a04ed9abbf20b00778dc43
출처 데이터셋
uspto-grants-2004_10
특허 번호
US06803368B2

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