4-Aminophenol → 4-(2-(Pyrrolidin-1-yl)ethoxy)aniline

HRID 1713633Notes

Reaction equation

HRID 1713633 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl.Cl[CH2:11][CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.[OH-].[Na+]>CN(C=O)C>[N:13]1([CH2:12][CH2:11][O:8][C:5]2[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 14798Sodium HydroxideHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

Product 1

HCID 64937494-(2-(Pyrrolidin-1-yl)ethoxy)aniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-aminophenol (4.0 g, 37.4 mmol), 1-(2-chloroethyl)-pyrrolidine hydrochloride (7.6 g, 44.9 mmol, 1.2 equiv), NaOH (3.7 g, 93.5 mmol, 2.5 equiv) in DMF (64 mL) is stirred for 2 h at 75° C., under an argon atmosphere. The mixture is allowed to cool to RT and then filtered through a glass sintered funnel. The filtrate is diluted with CH2Cl2 (200 mL), washed with brine (2×50 mL), dried (Na2SO4), filtered and concentrated. The residue is purified by silica gel (260 g) column chromatography (CH2Cl2/MeOH, 70/30→50/50) to afford the title compound as a dark brown oil: ES-MS: 207.1 [M+H]+; Rf=0.18 (CH2Cl2/MeOH, 50/50).

Workup

  1. temperatureto cool to RT
  2. filtrationfiltered through a glass sintered funnel
  3. additionThe filtrate is diluted with CH2Cl2 (200 mL)
  4. washwashed with brine (2×50 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is purified by silica gel (260 g) column chromatography (CH2Cl2/MeOH, 70/30→50/50)

Sources & evidence

ORD record
ord-a8b576ea3a2d4f27a7a3547d32554f72
Source dataset
uspto-grants-2010_09
Patent number
US07795288B2

Reaction notes

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