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

HRID 409655

반응식

HRID 409655 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 64847114-(2-Morpholinoethoxy)aniline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9031264226a141c2b99b317bd5426e8b
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759517B2

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