1-(4-Morpholinophenyl)-1-phenylprop-2-yn-1-ol → 6-Morpholino-3-(4-morpholinophenyl)-3-phenyl-3h-naphtho[2,1-b]pyran

HRID 1597119Notes

Reaction equation

HRID 1597119 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[C:9]([OH:17])[CH:8]=2)[CH2:3][CH2:2]1.[O:18]1[CH2:23][CH2:22][N:21]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)(O)[C:31]#[CH:32])=[CH:26][CH:25]=2)[CH2:20][CH2:19]1>C1(C)C=CC=CC=1>[O:1]1[CH2:2][CH2:3][N:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]3[CH:32]=[CH:31][C:30]([C:27]4[CH:28]=[CH:29][C:24]([N:21]5[CH2:20][CH2:19][O:18][CH2:23][CH2:22]5)=[CH:25][CH:26]=4)([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[O:17][C:9]=3[CH:8]=2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 2867411-(4-Morpholinophenyl)-1-phenylprop-2-yn-1-olHCID 109880424-Morpholino-2-naphthol

Product 1

HCID 98061486-Morpholino-3-(4-morpholinophenyl)-3-phenyl-3h-naphtho[2,1-b]pyranYield 73.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-morpholino-2-naphthol (1.5 g, 6.5 mmol) and 1(4-morpholinophenyl)-1-phenylprop-2-yn-1-ol (1.92 g, 6.5 mmol) in toluene (65 cm3) containing acidic alumina (Brockmann 1), (4.0 g) was refluxed for 60 minutes. The cooled solution was filtered and the alumina was washed well with EtOAc (200 cm3). Removal of the solvent from the filtrate gave an oil which solidified on standing at room temperature. Recrystallisation from EtOAc/hexane gave 6-morpholino-3(4-morpholinophenyl)-3-phenyl-3H-naphtho[2,1-b]pyran (yield=2.4 g, theoretical yield=3.3 g 73%, m.p.=187-188° C. (uncorrected), λmax in toluene=469 nm, i.e. red-orange).

Workup

  1. temperaturewas refluxed for 60 minutes
  2. filtrationThe cooled solution was filtered
  3. washthe alumina was washed well with EtOAc (200 cm3)
  4. customRemoval of the solvent from the filtrate
  5. customgave an oil which
  6. customon standing at room temperature
  7. customRecrystallisation from EtOAc/hexane

Sources & evidence

ORD record
ord-fc326a65b57c4e238aec0b91b55f99a2
Source dataset
uspto-grants-2001_09
Patent number
US06294112B1

Reaction notes

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