4-Methylmorpholine → N-[4-(4-Hydroxy-phenoxy)-benzyl]-propionamide

HRID 49152ノート

反応式

HRID 49152 の反応式
[NH2:1][CH2:2][C:3]1[CH:16]=[CH:15][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.CN1CCOCC1.[C:24](Cl)(=[O:27])[CH2:25][CH3:26]>C(#N)C>[OH:14][C:11]1[CH:12]=[CH:13][C:8]([O:7][C:6]2[CH:15]=[CH:16][C:3]([CH2:2][NH:1][C:24](=[O:27])[CH2:25][CH3:26])=[CH:4][CH:5]=2)=[CH:9][CH:10]=1

参加物

5

反応物 3

HCID 79724-MethylmorpholineHCID 62324Propionyl chlorideHCID 206362364-(4-Aminomethyl-phenoxy)-phenol

生成物 1

HCID 20636237N-[4-(4-Hydroxy-phenoxy)-benzyl]-propionamide

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 4-(4-Aminomethyl-phenoxy)-phenol (0.10 g, 0.47 mmol), MMP-resin (polystyrene bound N-methylmorpholine-type base, 0.30 g, 1.04 mmol) and 1.9 mL of acetonitrile was treated with propionyl chloride (0.086 mL, 1.0 mmol) and shaken for 24 hours at room temperature. After filtration of the resin, the filtrate was diluted with 2 mL of methanol and was treated with 2 mL of 1M lithium hydroxide (LiOH) in water. The mixture was shaken for 24 hours at room temperature, treated with Amberlite IRP-64® resin until neutral, filtered and concentrated in vacuo, affording N-[4-(4-Hydroxy-phenoxy)-benzyl]-propionamide. MS (m/z): 272.2 [M+H]+.

後処理

  1. filtrationAfter filtration of the resin
  2. additionthe filtrate was diluted with 2 mL of methanol
  3. additionwas treated with 2 mL of 1M lithium hydroxide (LiOH) in water
  4. stirringThe mixture was shaken for 24 hours at room temperature
  5. additiontreated with Amberlite IRP-64® resin until neutral,
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-75350c41cd7e499796319afe0614f444
出典データセット
uspto-grants-2004_03
特許番号
US06706723B2

反応ノート

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