Potassium Iodide → 2-(4-Morpholinophenyl)ethanol

HRID 2166162Notes

Reaction equation

HRID 2166162 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][O:14][CH2:15][CH2:16]Cl.C(N(CC)C(C)C)(C)C.[I-].[K+]>CN(C=O)C>[N:1]1([C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][CH:3]=2)[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8115Bis(2-chloroethyl) etherHCID 669044-Aminophenethyl alcoholHCID 81531Diisopropylethylamine

Product 1

HCID 135928032-(4-Morpholinophenyl)ethanolYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Aminobenzeneethanol (20.2 g), 2-chloroethyl ether (21.1 g), N,N-diisopropylethylamine (38.1 g) and potassium iodide (48.8 g) in DMF were heated to 80° under nitrogen for 60 h. The solvent was evaporated and the residue (~143 g) was purified by FCC eluting with ER-CX (1:1→1:0) to give the title compound as a pink-white solid (17.7 g) m.p. 57°.

Workup

  1. customThe solvent was evaporated
  2. customthe residue (~143 g) was purified by FCC
  3. washeluting with ER-CX (1:1→1:0)

Sources & evidence

ORD record
ord-d07af3a591da4c4198bfa5cbe1238b03
Source dataset
uspto-grants-1990_07
Patent number
US04943591

Reaction notes

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