Potassium Carbonate → HCID 11731847, compound

HRID 1379695Notes

Reaction equation

HRID 1379695 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[CH2:31][CH2:30][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)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 135493010HCID 135493010, compound

Product 1

HCID 11731847HCID 11731847, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The 2-(4-hydroxyphenyl)-3-(4-methoxyphenyl)-6-methylpyridine (4 g, 14 mmol), N-(2-chloroethyl)pyrrolidine hydrochloride (2.3 g, 14 mmol), and powdered K2CO3 (9.5 g, 68 mmol) were stirred in 250 mL methyl ethyl ketone and refluxed 18 h. The reaction mixture was worked up and purified by prep. chromatography (EtOH/ CH2Cl2 gradient), triturated with Et20, filtered, and dried in vacuo to give 3.7 g (71% yield) of white product: mp 63°-64° C.; 1H NMR (CDCl3) d 1.79-1.83 (comp, 4H, pyrrolidine), 2.60-2.64 (comp, 7H, Pyr-CH3 and pyrrolidine), 2.86-2.90 (t, 2H, J=6 Hz, NCH2), 3.81 (s, 3H, ArOCH3), 4.07-4.11 (t, 2H, J=6 Hz, OCH2), 6.78-6.82 (m, 4H, ArH), 7.06-7.30 (comp, 5H, ArH), 7.55-7.58 (d, 1H, J=8 Hz, ArH); MS(FD) 388(M+). Anal. Calcd for C25H28N202: C, 77.23; H, 7.26; N, 7.21. Found: C, 77.12; H, 7.48; N, 7.00.

Workup

  1. temperaturerefluxed 18 h
  2. custompurified by prep
  3. customchromatography (EtOH/ CH2Cl2 gradient), triturated with Et20
  4. filtrationfiltered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-ef3ec466dd014870929233e53baf543e
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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