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

HRID 392677ノート

反応式

HRID 392677 の反応式
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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ba16abdbd6a04ed9abbf20b00778dc43
出典データセット
uspto-grants-2004_10
特許番号
US06803368B2

反応ノート

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