Acetic Acid → (3,5-Bis-trifluoromethyl-benzyl)-[2-(4-cyclohexylmethyl-piperazin-1-yl)-quinolin-3-ylmethyl]-amine

HRID 577780

反応式

HRID 577780 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[CH2:6][NH2:7].[CH:17]1([CH2:23][N:24]2[CH2:29][CH2:28][N:27]([C:30]3[C:39]([CH:40]=O)=[CH:38][C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:31]=3)[CH2:26][CH2:25]2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[F:1][C:2]([F:15])([F:16])[C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:10]=1)[CH2:6][NH:7][CH2:40][C:39]1[C:30]([N:27]2[CH2:26][CH2:25][N:24]([CH2:23][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:29][CH2:28]2)=[N:31][C:32]2[C:37]([CH:38]=1)=[CH:36][CH:35]=[CH:34][CH:33]=2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 574868172-[4-(Cyclohexylmethyl)piperazin-1-yl]quinoline-3-carbaldehyde

生成物 1

HCID 57486818(3,5-Bis-trifluoromethyl-benzyl)-[2-(4-cyclohexylmethyl-piperazin-1-yl)-quinolin-3-ylmethyl]-amine収率 67.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3,5-Bis(trifluoromethyl)benzylamine (0.305 g, 1.25 mmol) was added to a solution of 2-(4-cyclohexylmethyl-piperazin-1-yl)-quinoline-3-carbaldehyde (0.4 g, 1.23 mmol) in methanol followed by acetic acid (0.15 mL) at ambient temperature under nitrogen atmosphere. After stirring 1 h, sodium cyanoborohydride (0.237 g, 3.77 mmol) was added carefully, and the reaction was stirred at RT for overnight. The reaction mixture was evaporated to dryness, and water (30 mL) and ethyl acetate (30 mL) were added to the residue, and this was then extracted with ethyl acetate (2×30 mL). The combined organic phases were washed with brine, dried over sodium sulfate, filtered, and concentrated under vacuum to afford a pale yellow crude product. Purification by silica gel column chromatography and eluting with 2.5% methanol/dichloromethane afforded the title compound (0.468 g), yield: 67%.

後処理

  1. stirringthe reaction was stirred at RT for overnight
  2. customThe reaction mixture was evaporated to dryness, and water (30 mL) and ethyl acetate (30 mL)
  3. additionwere added to the residue
  4. extractionthis was then extracted with ethyl acetate (2×30 mL)
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto afford a pale yellow crude product
  10. customPurification by silica gel column chromatography
  11. washeluting with 2.5% methanol/dichloromethane

出典と根拠

ORDレコード
ord-0a27e504c95b4d2dbe2f0f4bb93f117c
出典データセット
uspto-grants-2015_05
特許番号
US09040558B2

関連ノート

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