Potassium Hydroxide → HCID 13145802, compound

HRID 1074545Notes

Reaction equation

HRID 1074545 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1.Cl[CH2:20][CH2:21][CH2:22][N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C(O)C>[F:3][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:20][CH2:21][CH2:22][N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 958344-(3-Chloropropyl)morpholineHCID 13145801HCID 13145801, compound

Product 1

HCID 13145802HCID 13145802, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a solution of 0.56 g (0.01 mol) of potassium hydroxide in 18 ml of absolute ethanol are added 2.18 g (0.01 mol) of 4-(3-fluorobenzyloxy)phenol. There is then added a solution of 1.64 g (0.01 mol) of N-(3-chloropropyl)morpholine in 2 ml of absolute ethanol. The mixture is stirred at reflux for 24 hours, allowed to cool and then refrigerated. The solid which forms is collected by filtration, washed with absolute ethanol and dissolved in diethyl ether. The ethereal solution is washed consecutively with water (20 ml), 10% aqueous sodium hydroxide (3×15 ml) and water until neutral to litmus. The solution is dried over sodium sulfate, filtered and evaporated and recrystallized from diethyl ether-petroleum ether and from diethyl ether alone to yield N-[3-(4-{3-fluorobenzyloxy}phenoxy)propyl]morpholine.

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureto cool
  3. filtrationThe solid which forms is collected by filtration
  4. washwashed with absolute ethanol
  5. dissolutiondissolved in diethyl ether
  6. washThe ethereal solution is washed consecutively with water (20 ml), 10% aqueous sodium hydroxide (3×15 ml) and water until neutral to litmus
  7. dry with materialThe solution is dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customrecrystallized from diethyl ether-petroleum ether and from diethyl ether alone

Sources & evidence

ORD record
ord-c72717f097ab4d5d86c01c5367f111de
Source dataset
uspto-grants-1983_07
Patent number
US04393061

Reaction notes

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