Benzaldehyde → 2-(Benzylamino)-1-phenylethanol

HRID 72862ノート

反応式

HRID 72862 の反応式
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[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][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

5

反応物 3

HCID 240BenzaldehydeHCID 1000PhenylethanolamineHCID 4311764Sodium borohydride

生成物 1

HCID 2297462-(Benzylamino)-1-phenylethanol収率 70.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2-amino-1-phenyl-ethanol (12.0 g, 87.48 mmol) in methanol (60 mL) was added benzaldehyde (9.3 g, 8.9 mL, 87.48 mmol) and the reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was then cooled to 0° C. and sodium borohydride (3.3 g, 87.48 mmol) was added. The reaction mixture was gradually allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated in vacuo, diluted with water, and filtered. The residue was rinsed with cold isopropanol (3×), then dried in vacuo to give 2-(benzylamino)-1-phenylethanol as white crystals (14.0 g, 70%). ESI-MS m/z calc. 227.1. Found 228.2 (M+1)+; Retention time:0.8 minutes (3 min run). 1H NMR (400 MHz, MeOD) δ 7.37-7.27 (m, 8H), 7.27-7.19 (m, 2H), 4.78 (dd, J=8.5, 4.5 Hz, 1H), 3.77 (q, J=13.0 Hz, 2H), 2.82-2.68 (m, 2H).

後処理

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred overnight
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. additiondiluted with water
  6. filtrationfiltered
  7. washThe residue was rinsed with cold isopropanol (3×)
  8. customdried in vacuo

出典と根拠

ORDレコード
ord-aed35b26e3794dc99f4e65ea0289b1f7
出典データセット
uspto-grants-2014_09
特許番号
US08828996B2

反応ノート

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