3-Aminophenol → HCID 21941695, compound

HRID 1374660Notes

Reaction equation

HRID 1374660 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-15ccd38bd9aa48cb8e6142b6480ef748
Source dataset
uspto-grants-2007_01
Patent number
US07166601B2

Reaction notes

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