Hydrochloric Acid → (2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-{3-[3-(2-methylamino-ethyl)-phenoxy]-propyl}-amine hydrochloride salt

HRID 902693ノート

反応式

HRID 902693 の反応式
[Cl:1][C:2]1[C:38]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:11]=[C:12]([CH2:16][C:17]([NH:19][CH3:20])=O)[CH:13]=[CH:14][CH:15]=1.Cl>C1COCC1>[ClH:1].[Cl:1][C:2]1[C:38]([C:39]([F:40])([F:41])[F:42])=[CH:37][CH:36]=[CH:35][C:3]=1[CH2:4][N:5]([CH2:21][CH:22]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH2:17][NH:19][CH3:20])[CH:11]=1

参加物

4

反応物 2

HCID 313Hydrochloric Acid2 回HCID 117646132-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-N-methyl-acetamide2 回

生成物 1

HCID 69253092(2-Chloro-3-trifluoromethyl-benzyl)-(2,2-diphenyl-ethyl)-{3-[3-(2-methylamino-ethyl)-phenoxy]-propyl}-amine hydrochloride salt収率 99.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirring solution of 2-(3-{3-[(2-chloro-3-trifluoromethyl-benzyl)-diphenylethyl-amino]-propoxy}-phenyl)-N-methyl-acetamide (101 mg, 0.17 mmol) (Intermediate 3 above) in anhydrous THF (10 mL) was added BH3 THF (0.34 ml, 1 M solution in THF). The resulting solution was then heated to reflux for 1.5 hours. Aqeous HCl (0.34 ml. 6 M) was then added to the reaction and the mixture was heated at reflux for 30 min. After cooling to RT, the reaction mixture was concentrated in vacuo and extracted with EtOAc (3×). The combined organic layers were washed with brine (1×), dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by column chromatography over silica gel (silica gel 60, EM science) using 5% MeOH:dichloro-methane as eluent. The free base was dissolved in dichloromethane, 1 eq. of HCl (1M in Et2O) was added, and the mixture was evaporated to afford the title compound as a white solid (52 mg, 50%). MS(ES) m/e 581.4 (M+).

後処理

  1. temperatureThe resulting solution was then heated
  2. temperatureto reflux for 1.5 hours
  3. temperaturethe mixture was heated
  4. temperatureat reflux for 30 min
  5. concentrationthe reaction mixture was concentrated in vacuo
  6. extractionextracted with EtOAc (3×)
  7. washThe combined organic layers were washed with brine (1×)
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was purified by column chromatography over silica gel (silica gel 60, EM science)
  12. dissolutionThe free base was dissolved in dichloromethane
  13. customthe mixture was evaporated

出典と根拠

ORDレコード
ord-dae9fb5583e441ceb973b483352627a8
出典データセット
uspto-grants-2008_04
特許番号
US07365085B2

反応ノート

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