Acetic Acid → 4-((Morpholin-4-yl)methyl)benzonitrile

HRID 1190999

反応式

HRID 1190999 の反応式
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1)#[N:2].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(O)(=O)C.C([BH3-])#N.[Na+]>ClCCCl>[N:11]1([CH2:7][C:6]2[CH:9]=[CH:10][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 660424-CyanobenzaldehydeHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 2168644-((Morpholin-4-yl)methyl)benzonitrile収率 79.2%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Dissolve 4-cyanobenzaldehyde (5 g, 38.1 mmol), morpholine (4.15 g, 47.7 mmol) and acetic acid (2.2 mL, 38.1 mmol) in DCE (100 mL). Add sodium cyanoborohydride (3.59 g, 57.2 mmol), and stir the mixture overnight. Add water (100 mL), separate the layers and extract the aqueous layer with DCM (3×50 mL). Wash the combined organic extracts with brine, dry over Na2SO4, filter and concentrate in vacuo. Purify by chromatography on silica gel (80 g, pre-packed cartridge) eluting with hexane/EtOAc (1:0 to 1:2 over 1.25 h, 80 mL/min) to obtain the desired intermediate as a colorless oil (6.1 g, 79%). MS (APCI+) m/z: 203 (M+H)+.

後処理

  1. customAdd water (100 mL), separate the layers
  2. extractionextract the aqueous layer with DCM (3×50 mL)
  3. washWash the combined organic extracts with brine
  4. dry with materialdry over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo
  7. customPurify by chromatography on silica gel (80 g, pre-packed cartridge)
  8. washeluting with hexane/EtOAc (1:0 to 1:2 over 1.25 h, 80 mL/min)

出典と根拠

ORDレコード
ord-58e7650f2a8a4da5968718530d568faf
出典データセット
uspto-grants-2014_03
特許番号
US08680091B2

関連ノート

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