Potassium Iodide → 4-(4-Morpholinyl)benzenebutanol

HRID 568882Notes

Reaction equation

HRID 568882 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:4][CH:3]=1.Cl[CH2:14][CH2:15][O:16][CH2:17][CH2:18]Cl.[I-].[K+]>CN(C=O)C>[N:1]1([C:2]2[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[CH:6][CH:7]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 8115Bis(2-chloroethyl) etherHCID 150062264-(4-Aminophenyl)butan-1-OL

Product 1

HCID 200298274-(4-Morpholinyl)benzenebutanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-aminobenzenebutanol (7.5), 2-chloroethyl ether (6.5 g, 5.32 ml), DEA (11.74 g) and finely ground potassium iodide (15.0 g) was stirred in DMF (500 ml) at 100° under nitrogen for 65 h. The mixture was cooled, the solvent removed in vacuo at 55° and the residue partitioned between EA (250 ml) and water (100 ml). The aqueous layer was extracted with further EA (100 ml), the combined organic solutions washed with brine (150 ml), dried and evaporated onto FCC silica (15 g). The impregnated material was applied to an FCC column, elution with ER-CX (2:1) affording the title compound as a waxy cream solid (6.13 g) m.p. 51°-52°.

Workup

  1. temperatureThe mixture was cooled
  2. customthe solvent removed in vacuo at 55°
  3. customthe residue partitioned between EA (250 ml) and water (100 ml)
  4. extractionThe aqueous layer was extracted with further EA (100 ml)
  5. washthe combined organic solutions washed with brine (150 ml)
  6. customdried
  7. customevaporated onto FCC silica (15 g)
  8. washThe impregnated material was applied to an FCC column, elution with ER-CX (2:1)

Sources & evidence

ORD record
ord-adb2db975a8444aaa395b835168be124
Source dataset
uspto-grants-1988_03
Patent number
US04730008

Reaction notes

Loading…