Hydrochloric Acid → HCID 18966366, compound

HRID 2226108Notes

Reaction equation

HRID 2226108 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:16][CH2:15]1.[CH:28](=[O:37])[C:29]1[C:30]([O:35][CH3:36])=[CH:31][CH:32]=[CH:33][CH:34]=1.Cl>C1COCC1.C(O)(C)C.O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][C:22]2[C:27]([CH:28]([OH:37])[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])=[CH:26][CH:25]=[CH:24][N:23]=2)[CH2:16][CH2:15]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 86582-MethoxybenzaldehydeHCID 199286Piperazine, 1-(o-methoxyphenyl)-4-(2-(2-pyridyl)ethyl)-HCID 178418339Butyllithium

Product 1

HCID 18966366HCID 18966366, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

n-Butyl-lithium (1.6M solution in hexane) (7.0 ml, 11.2 mmol, 1.1 equiv.) was added dropwise at below -60° C. to a solution of 1-(2-methoxyphenyl)-4-(2-pyridylethyl)piperazine base (3.00 g, 10.1 mmol) in anhydrous THF (20 ml). The resulting orange-red solution was stirred for a further 0.25 h at -70° C. then quenched with a solution of ortho-anisaldehyde (1.5 g, 11.0 mmol) in anhydrous THF (2 ml). The reaction mixture was poured into water (50 ml) and extracted with dichloromethane (2×75 ml). The organic extract was washed (brine), dried (Na2SO4) and concentrated in vacuo. The residue was subjected to chromatography (SiO2 :Et2O) to give the first Rf diastereoisomer as a white foam which was dissolved in isopropanol (20 ml) and acidified with ethanolic hydrogen chloride to afford the first diastereoisomer of the title compound as the trihydrochloride (227 mg), m.p. 140°-145° C. (Found: C,57.7;H,6.5;N,7.8 C26H31N3O3.3HCl requires C,57.5;H,6.3;N,7.7%).

Workup

  1. extractionextracted with dichloromethane (2×75 ml)
  2. extractionThe organic extract
  3. washwas washed (brine)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give the first Rf diastereoisomer as a white foam which

Sources & evidence

ORD record
ord-f2564d9371f24ee9b7f9e11caa00f9fa
Source dataset
uspto-grants-1994_09
Patent number
US05346896

Reaction notes

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