Ethanol → N-(2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyl)(3.5 bis(trifluoromethyl)phenyl)methanamine

HRID 2075078

反応式

HRID 2075078 の反応式
[CH3:1][O:2][C:3]1([C:10]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:11]=2[CH:12]=O)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[F:22][C:23]([F:37])([F:36])[C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:27][NH2:28].C(O)C.[BH4-].[Na+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1([C:10]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:11]=2[CH2:12][NH:28][CH2:27][C:26]2[CH:29]=[C:30]([C:32]([F:33])([F:34])[F:35])[CH:31]=[C:24]([C:23]([F:22])([F:36])[F:37])[CH:25]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

参加物

6

反応物 4

HCID 702EthanolHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 4311764Sodium borohydrideHCID 589686662-(1-Methoxycycloheptyl)-5-(trifluoromethyl)benzaldehyde

生成物 1

HCID 58968635N-(2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzyl)(3.5 bis(trifluoromethyl)phenyl)methanamine

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 2-(1-methoxycycloheptyl)-5-(trifluoromethyl)benzaldehyde (167 mg; 0.556 mmol) and 3,5-bistrifluoromethyl benzylamine (150 mg; 0.616 mmol) in toluene (4 mL) was heated at reflux for 16 hours, after which solvent was removed. Ethanol (4 mL) and sodium borohydride (31 mg; 0.819 mmol) were added to the residue. The resulting mixture was stirred at room temperature for 16 hours. Solvent was evaporated under reduced pressure. The residue was taken up in ethyl acetate and washed twice with water and dried over sodium sulfate and concentrated under reduced pressure. The residue was purified over a 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-25% ethyl acetate in heptane) to yield 194 mg (66.1% for 2 steps) of the title compound as a gum. MS (ES+): Calc: 527.4 Found: 528.4 (M+H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customafter which solvent was removed
  4. customSolvent was evaporated under reduced pressure
  5. washwashed twice with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified over a 12 g RediSep column (Teledyne Isco Inc., Lincoln Nebr.) (eluted with 5-25% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-72d47ceaaa514ea5bad709e2a8ab24c6
出典データセット
uspto-grants-2011_04
特許番号
US07919506B2

関連ノート

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