Hydrochloric Acid → N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydrochloride

HRID 410148

反応式

HRID 410148 の反応式
[Cl:1][CH:2]=[CH:3][CH2:4][NH:5][C@@H:6]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1)[CH3:7].CN1CCCC1=O.[F:25][C:26]([F:36])([F:35])[C:27]1[CH:28]=[C:29]([Mg]Br)[CH:30]=[CH:31][CH:32]=1.Cl>O1CCCC1.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.C/C(/[O-])=C/C(C)=O.[Fe+3].C1(C)C=CC=CC=1.O>[ClH:1].[C:8]1([C@H:6]([NH:5][CH2:4][CH:3]=[CH:2][C:31]2[CH:30]=[CH:29][CH:28]=[C:27]([C:26]([F:36])([F:35])[F:25])[CH:32]=2)[CH3:7])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][CH:9]=1

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 13387N-methyl-2-pyrrolidoneHCID 866746003-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amineHCID 178506173HCID 178506173、化合物

生成物 1

HCID 67057068N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydrochloride収率 70.23%

試薬・触媒・溶媒 4

HCID 5483663Ferric acetylacetonate触媒HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
2.5 °C

実験手順

A solution of 3-chloro-N-[(1R)-1-(naphthalen-1-yl)ethyl]prop-2-en-1-amine (Example 1; 50 g), iron acetylacetonate (3.6 g) and N-methyl-2-pyrrolidone (1.0 g) in tetrahydrofuran (200 mL) at 0 to −5° C. was added to a solution of 3-(trifluoromethyl)phenyl magnesium bromide (Example 3) in tetrahydrofuran (150 mL) at −25° C. to −30° C. under inert atmosphere. The reaction mixture was stirred at 0 to 5° C. for 15 to 20 minutes. After the completion of the reaction, de-ionized water (75 mL) was added at 0 to 10° C. Toluene (250 mL) was added to the reaction mixture and the pH of mixture was adjusted to 0 to 1 using hydrochloric acid (6 Normal; 250 mL) at 10° C. to 35° C. and stirred at the same temperature for about 15 minutes. Layers were separated, and the organic layer was washed with de-ionized water (2×250 mL) and concentrated under vacuum at 55° C. to 60° C. Isopropyl alcohol (125 mL) was added to the residue obtained and heated to 40° C. to 45° C. to get a clear solution. The solution was cooled to 20° C. to 30° C. and stirred for about 2 hours to give solid. The solid was filtered, washed with isopropyl alcohol (2×50 mL) and dried under vacuum at 45° C. to 50° C. to give N-[(1R)-1-(naphthalen-1-yl)ethyl]-3-[3-(trifluoromethyl)phenyl]prop-2-en-1-amine hydrochloride.

後処理

  1. additionwas added at 0 to 10° C
  2. stirringstirred at the same temperature for about 15 minutes
  3. customLayers were separated
  4. washthe organic layer was washed with de-ionized water (2×250 mL)
  5. concentrationconcentrated under vacuum at 55° C. to 60° C
  6. additionIsopropyl alcohol (125 mL) was added to the residue
  7. customobtained
  8. temperatureheated to 40° C. to 45° C.
  9. customto get a clear solution
  10. temperatureThe solution was cooled to 20° C. to 30° C.
  11. stirringstirred for about 2 hours
  12. customto give solid
  13. filtrationThe solid was filtered
  14. washwashed with isopropyl alcohol (2×50 mL)
  15. customdried under vacuum at 45° C. to 50° C.

出典と根拠

ORDレコード
ord-fd33f366fd014808864afa8f7fd108dd
出典データセット
uspto-grants-2014_06
特許番号
US08759586B2

関連ノート

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