Hydrochloric Acid → HCID 18923793, compound

HRID 1379698Notes

Reaction equation

HRID 1379698 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][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:9]=2)=[CH:4][CH:3]=1.Cl.Cl[CH2:32][CH2:33][N:34]1[CH2:38][CH2:37][CH2:36][CH2:35]1.C([O-])([O-])=O.[K+].[K+].Cl>C(C(C)=O)C.CCO.C(Cl)Cl>[N:34]1([CH2:33][CH2:32][O:1][C:2]2[CH:7]=[CH:6][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:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[N:9]=3)=[CH:4][CH:3]=2)[CH2:38][CH2:37][CH2:36][CH2:35]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride2×HCID 136207703HCID 136207703, compound

Product 1

HCID 18923793HCID 18923793, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 21584144Dichloromethane ethanolSolvent

Procedure

The 2-(4-hydroxyphenyl)-3,6-bis(4-methoxyphenyl)pyridine (2.3 g, 6 mmol), N-(2-chloroethyl)pyrrolidine hydrochloride (1.1 g, 6 mmol), and powdered K2CO3 (4.1 g, 30 mmol) were stirred in 250 mL methyl ethyl ketone and refluxed 18 h. The TLC (EtOH/ CH2Cl2, 1:4) of the reaction mixture indicated some starting material remained, so more N-(2-chloroethyl)pyrrolidine hydrochloride (0.3 g, 1.6 mmol) and K2 CO3 (2 g, 15 mmol) were added and reaction mixture refluxed an additional 18 h. The reaction mixture was worked up, concentrated, and the residue was dissolved in 25 mL MeOH, treated with 5 mL HCl/ MeOH at 0° C., and concentrated. The residue was recrystallised from MeOH/ Et2O to give 1.8 g (58% yield) of product as the HCl salt: mp 230°-231° C.; 1H NMR (CDCl3) d 1.61 (bs, 2H, pyrrolidine), 2.10-2.26 (comp, 4H, pyrrolidine), 2.90-3.10 (bs, 2H, pyrrolidine), 3.48 (bs, 2H, NCH2), 3.84 (s, 3H, ArOCH3), 3.88 (s, 3H, ArOCH3), 4.10-4.14 (m, 2H, OCH2), 6.78-6.81 (d, 2H, J=9 Hz, ArH), 6.86-6.89 (d, 2H, J=9 Hz, ArH), 7.00-7.03 (d, 2H, J=9 Hz, ArH), 7.14-7.16 (d, 2H, J=9 Hz, ArH), 7.44-7.46 (d, 2H, J=9 Hz, ArH), 7.66-7.73 (m, 2H, ArH), 8.07-8.10 (d, 2H, J=9 Hz, ArH); MS(FD) 480(M+). Anal. Calcd for C31H32N2O3HCl: C, 72.01; H, 6.43; N, 5.42. Found: C, 72.02; H, 6.65; N, 5.24.

Workup

  1. temperaturerefluxed 18 h
  2. customreaction mixture
  3. temperaturerefluxed an additional 18 h
  4. concentrationconcentrated
  5. dissolutionthe residue was dissolved in 25 mL MeOH
  6. additiontreated with 5 mL HCl/ MeOH at 0° C.
  7. concentrationconcentrated
  8. customThe residue was recrystallised from MeOH/ Et2O

Sources & evidence

ORD record
ord-c10a0f65640d431bb817e726e46c7cb6
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

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