4-Aminophenol → 4-(2-Morpholinoethoxy)aniline

HRID 409655

反応式

HRID 409655 の反応式
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.[OH-].[Na+]>CN(C=O)C>[N:5]1([CH2:4][CH2:3][O:18][C:15]2[CH:16]=[CH:17][C:12]([NH2:11])=[CH:13][CH:14]=2)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

参加物

5

反応物 3

HCID 4034-AminophenolHCID 14798Sodium HydroxideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)

生成物 1

HCID 64847114-(2-Morpholinoethoxy)aniline

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4-(2-Chloro-ethyl)-morpholine hydrochloride (4.2 g, 22 mmol, 1.2 equiv) is added in one portion to a mixture of 4-aminophenol (2 g, 18.3 mmol) and finely powdered sodium hydroxide (1.87 g, 45.8 mmol, 2.5 equiv) in DMF (32 mL), under an argon atmosphere. The reaction mixture is stirred for 23.5 h at RT. The resulting dark suspension is filtered. The filtrate is diluted with DCM (200 ml) and washed with brine (2×60 mL). The organic phase is dried (sodium sulfate), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/EtOH, 95:5→7:3) provides the title compound as a yellow-brown solid: API-MS: 223.2 [MH]+; TLC: Rf=0.31 (DCM/EtOH, 9:1).

後処理

  1. filtrationThe resulting dark suspension is filtered
  2. additionThe filtrate is diluted with DCM (200 ml)
  3. washwashed with brine (2×60 mL)
  4. dry with materialThe organic phase is dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by silica gel column chromatography (DCM/EtOH, 95:5→7:3)

出典と根拠

ORDレコード
ord-9031264226a141c2b99b317bd5426e8b
出典データセット
uspto-grants-2014_06
特許番号
US08759517B2

関連ノート

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