Benzaldehyde → 4-(2-(Benzylamino)ethyl)phenol

HRID 130719

反応式

HRID 130719 の反応式
[NH2:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[CH:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[BH4-].[Na+]>CO>[CH2:11]([NH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 5610TyramineHCID 4311764Sodium borohydride

生成物 1

HCID 30425724-(2-(Benzylamino)ethyl)phenol収率 91%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

Combine tyramine (5.0 g, 36.4 mmol), benzaldehyde (3.8 ml, 37.2 mmol) in MeOH (46 mL), heat at reflux for 2 h. Cool the mixture at 0° C. and add NaBH4 (1.44 g, 38.2 mmol). Stir at room temperature overnight. Remove most of MeOH, add H2O and stir for 2 h. Filter the mixture and wash the white solid with water. Dry the solid precipitate under vacuum at 40° C. overnight to afford the title compound (7.53 g, 91%). Electrospray MS M+1 ion=228, 1H-NMR (methanol-d4, 300 MHz): 7.40-7.20 (m, 5H), 7.03-6.95 (m, 2H), 6.73-6.65 (m, 2H), 3.75 (s, 2H), 2.85-2.65 (m, 4H).

後処理

  1. temperatureat reflux for 2 h
  2. customRemove most of MeOH
  3. additionadd H2O
  4. stirringstir for 2 h
  5. filtrationFilter the mixture
  6. washwash the white solid with water
  7. customDry the solid precipitate under vacuum at 40° C. overnight

出典と根拠

ORDレコード
ord-fc04a3f8bde344ae868e000a15d9d614
出典データセット
uspto-grants-2008_06
特許番号
US07381719B2

関連ノート

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