Potassium Carbonate → HCID 18923790, compound

HRID 1379697Notes

Reaction equation

HRID 1379697 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]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:30][CH2:31][N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.C([O-])([O-])=O.[K+].[K+]>C(C(C)=O)C>[N:32]1([CH2:31][CH2:30][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]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:9]=3)=[CH:6][CH:7]=2)[CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 136144409HCID 136144409, compound

Product 1

HCID 18923790HCID 18923790, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The 2-(4-hydroxyphenyl)-3-(4-methoxyphenyl)-6-phenylpyridine (2.0 g, 5 mmol), N-(2-chloroethyl)pyrrolidine hydrochloride (1.0 g, 5 mmol), and powdered K2CO3 (4.2 g, 30 mmol) were stirred in 200 mL methyl ethyl ketone and refluxed 20 h. The reaction mixture was worked up and the residue triturated with pet. ether, filtered, and dried in vacuo to give 2.1 g (84% yield) of an off-white solid: mp 100°-103° C.; 1H NMR (CDCl3) d 1.81-1.84 (m, 4H, pyrrolidine), 2.61-2.65 (m, 4H, pyrrolidine), 2.88-2.92 (t, 2H, J=6 Hz, NCH2), 3.83 (s, 3H, ArOCH3), 4.10-4.14 (t, 2H, J=6 Hz, OCH2), 6.81-6.87 (m, 4H, ArH), 7.15-7.18 (d, 2H, J=9 Hz, ArH) 7.42-7.50 (m, 5H, ArH), 7.73 (s, 2H, ArH), 8.13-8.16 (d, 2H, J=9 Hz, ArH); MS(FD) 450(M+). Anal. Calcd for C30H30N2O2 : C, 79.97; H, 6.71; N, 6.22. Found: C, 79.86; H, 6.09; N, 6.16.

Workup

  1. temperaturerefluxed 20 h
  2. customthe residue triturated with pet. ether
  3. filtrationfiltered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-b6a8b0a54b7d477ca37a9114f22fba8e
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

Loading…