Morpholine → HCID 21393726, compound

HRID 461451Notes

Reaction equation

HRID 461451 reaction equation
[Br-].[CH2:2]([N+:4]1([CH2:17][CH3:18])[CH2:12][C:11]2[CH:10]=[C:9]3[CH:13]=[CH:14][CH:15]=[CH:16][C:8]3=[CH:7][C:6]=2[CH2:5]1)[CH3:3].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1>>[CH2:2]([N:4]([CH2:5][C:6]1[C:11]([CH2:12][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)=[CH:10][C:9]2[C:8](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1)[CH2:17][CH3:18])[CH3:3]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 44658157HCID 44658157, compound

Product 1

HCID 21393726HCID 21393726, compound

Procedure

2,2-Diethylbenz[f]isoindolinium bromide (13 g) was refluxed with morpholine (150 ml) for 30 hr. Morpholine was evaporated and the residue was partitioned between sodium hydroxide solution and ether; the ether layer was evaporated to dryness and the residue purified by chromatography [eluent, diethylamine:cyclohexane = 1:4, silica (250 g)] and distillation to give 2-diethylaminomethyl-3-morpholinomethylnaphthalene, b.p. 160°/0.015 mm.

Workup

  1. customMorpholine was evaporated
  2. customthe residue was partitioned between sodium hydroxide solution and ether
  3. customthe ether layer was evaporated to dryness
  4. distillationthe residue purified by chromatography [eluent, diethylamine:cyclohexane = 1:4, silica (250 g)] and distillation

Sources & evidence

ORD record
ord-f9b5fa629ce3460b9a2170bba00c5af6
Source dataset
uspto-grants-1977_12
Patent number
US04062955

Reaction notes

Loading…