Hydrochloric Acid → HCID 9889249, compound

HRID 1379704Notes

Reaction equation

HRID 1379704 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:20]([C:21]4[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=4)=[CH:19][CH:18]=[C:17]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:16]=3)=[CH:11][CH:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.B(Cl)(Cl)Cl.CCO.C(Cl)Cl>ClCCCl>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[CH:11][C:12]([C:15]3[C:20]([C:21]4[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=4)=[CH:19][CH:18]=[C:17]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:16]=3)=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25135Boron Trichloride2×HCID 18923790HCID 18923790, compoundHCID 21584144Dichloromethane ethanol

Product 1

HCID 9889249HCID 9889249, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

The 2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]-3-(4-methoxyphenyl)-6-phenylpyridine as the HCl salt (1.9 g, 3.9 mmol) was slurried with 50 mL of DCE in a screw cap flask, cooled to 0° C., and stirred while the BCl3 (2.7 mL at 0° C., 32 mmol) in 5 mL DCE was added and the reaction flask sealed. After 2 h, TLC (EtOH/ CH2Cl2, 1:4) indicated that starting material remained, so an additional 1.7 mL of BCl3 (20 mmol) was added and reaction mixture stirred for 18 h. The reaction mixture was carefully quenched with 25 mL MeOH at 0° C., poured in 150 mL of aqueous NaHCO3, and extracted with CH2Cl2 (3×100 mL). The CH2Cl2 extracts were combined, washed with brine, dried (Na2SO4), concentrated, and recrystallised from EtOH to give 1.35 g (79 % yield) of product: mp 176°-178° C.; 1H NMR (CDCl3) d 1.86 (bs, 4H, pyrrolidine), 2.73(bs, 4H, pyrrolidine), 2.97-3.01 (t, 2H, J=5 Hz, CH2N), 4.12-4.16 (t, 2H, J=5 Hz, OCH2), 6.64-6.67 (m, 4H, ArH), 6.98-7.01 (d, 2H, J=8 Hz, ArH), 7.38-7.50 (m, 5H, ArH), 7.67 (s, 2H, ArH), 8.10-8.12 (d, 2H, J=8 Hz, ArH); MS(FD) 436 (M+). Anal. Calcd for C29H28N2O2 : C, 79.79; H, 6.46; N, 6.42. Found: C, 80.01; H, 6.55; N, 6.54.

Workup

  1. customcap flask
  2. additionwas added
  3. customthe reaction flask sealed
  4. customreaction mixture
  5. customThe reaction mixture was carefully quenched with 25 mL MeOH at 0° C.
  6. additionpoured in 150 mL of aqueous NaHCO3
  7. extractionextracted with CH2Cl2 (3×100 mL)
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customrecrystallised from EtOH

Sources & evidence

ORD record
ord-2a629e7219c24d8eb7ceb0645682de0d
Source dataset
uspto-grants-1997_09
Patent number
US05672609

Reaction notes

Loading…