Water → N-Ethyl-4-chlorobenzylamine

HRID 408585ノート

反応式

HRID 408585 の反応式
[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH2:10]([NH2:12])[CH3:11].O.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][NH:12][CH2:10][CH3:11])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 962WaterHCID 6341EthylamineHCID 77264-ChlorobenzaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 580651N-Ethyl-4-chlorobenzylamine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
20 °C

実験手順

To a solution of 4-chlorobenzaldehyde (1 eq.) in MeOH was added ethylamine 70% in water (10 eq.). The reaction was stirred for 15 h at 20° C. under argon then NaBH4 (2 eq.) was added. The reaction was stirred at 20° C. for 5 h. The reaction was quenched with water then acidified with aqueous HCl (2M). The aqueous layer was washed with EtOAc. The organic layer was discarded. Aqueous NaOH (2M) was then added to the aqueous layer until pH=10 and the crude was extracted twice with EtOAc. The organic layers were combined, dried over MgSO4, filtered and concentrated under reduced pressure to afford (4-chloro-benzyl)-ethyl-amine.

後処理

  1. stirringThe reaction was stirred at 20° C. for 5 h
  2. customThe reaction was quenched with water
  3. washThe aqueous layer was washed with EtOAc
  4. additionAqueous NaOH (2M) was then added to the aqueous layer until pH=10
  5. extractionthe crude was extracted twice with EtOAc
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-9cbdd250aa5e45388d9c0e02b231ef54
出典データセット
uspto-grants-2014_06
特許番号
US08759334B2

反応ノート

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