3-Aminophenol → HCID 21941695, compound

HRID 1063781Notes

Reaction equation

HRID 1063781 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl.Cl[CH2:13][CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][N:16]1[CH3:20]>CN(C=O)C>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:13][CH2:14][CH:15]1[CH2:19][CH2:18][CH2:17][N:16]1[CH3:20]

Participants

5

Reactant 3

HCID 115683-AminophenolHCID 24758Sodium hydrideHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)

Product 1

HCID 21941695HCID 21941695, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-aminophenol (0.74 g, 6.8 mmol) in DMF (10 ml) was added dropwise to 95% NaH (0.49 g, 20.4 mmol) in 10 ml DMF at 0° C., under nitrogen. The reaction was stirred until H2(g) evolution ceased. 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (1.25 g, 6.8 mmol) was then added portionwise. The mixture was stirred at room temperature for 18 h. The reaction mixture was quenched with 1N NaOH (50 ml) and the desired product extracted into ether (3×50 ml). The combined ether layers were washed (2×50 ml) with water, dried over MgSO4, and evaporated to dryness in vacuo. The residue was purified on silica gel by flash chromatography using 2% TEA in ethyl acetate to give an oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 h
  2. customThe reaction mixture was quenched with 1N NaOH (50 ml)
  3. extractionthe desired product extracted into ether (3×50 ml)
  4. washThe combined ether layers were washed (2×50 ml) with water
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness in vacuo
  7. customThe residue was purified on silica gel by flash chromatography
  8. customto give an oil

Sources & evidence

ORD record
ord-37eaca7a6b53423abe3e9aca1559a789
Source dataset
uspto-grants-2005_11
Patent number
US06967199B2

Reaction notes

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