Potassium Carbonate → HCID 18923791, compound

HRID 1379696Notes

Reaction equation

HRID 1379696 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[CH:12][CH:11]=[C:10]([CH3:22])[N:9]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.C([O-])([O-])=O.[K+].[K+]>C(C(C)=O)C>[N:27]1([CH2:26][CH2:25][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[C:13]([C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)=[CH:12][CH:11]=[C:10]([CH3:22])[N:9]=3)=[CH:6][CH:7]=2)[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 135493010HCID 135493010, compound

Product 1

HCID 18923791HCID 18923791, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The 2-(4-hydroxyphenyl)-3-(4-methoxyphenyl)-6-methylpyridine (3.0 g, 10 mmol), N-(2-chloroethyl)morpholine hydrochloride (1.9 g, 10 mmol), and powdered K2CO3 (7.1 g, 51 mmol) were stirred in 200 mL methyl ethyl ketone and refluxed 20 h. The reaction mixture was worked up and purified by prep. chromatography (EtOH/ CH2Cl2 gradient), triturated with Et2O/ pet. ether, filtered, and dried in vacuo to give 3.4 g (82% yield) of white solid: mp 66°-67° C.; 1H NMR (CDCl3) d 2.55-2.58 (m 4H, morpholine), 2.62 (s, 3H, pyr-CH3), 2.76-2.80 (t, 2H, J=6 Hz, NCH2), 3.72-3.75 (m, 4H, morpholine), 3.80 (s, 3H, ArOCH3), 4.06-4.10 (t, 2H, J=6 Hz, OCH2), 6.75-6.81 (m, 4H, ArH), 7.05-7.14 (m, 4H, ArH), 7.26-7.29 (m, 1H, ArH) 7.54-7.56 (d, 1H, J=8 Hz, ArH); MS(FD) 404(M+). Anal. Calcd for C25H28N2O3 : C, 74.23; H, 6.98; N, 6.93. Found: C, 74.50; H, 6.91; N, 7.05.

Workup

  1. temperaturerefluxed 20 h
  2. custompurified by prep
  3. customchromatography (EtOH/ CH2Cl2 gradient), triturated with Et2O/ pet. ether
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-85f498d4a134477fb8dee157cd70440f
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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