Hydrochloric Acid → 1-[2-(3,4-dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(3,5-dimethoxyphenyl)piperazine dihydrochloride

HRID 1110793Notes

Reaction equation

HRID 1110793 reaction equation
Br[CH2:2][CH2:3][CH:4]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[O:7][CH2:6][CH2:5]1.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[ClH:38]>CC(=O)CC.C(O)(C)C.C(O)C>[ClH:38].[ClH:38].[O:7]1[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:4]([CH2:3][CH2:2][N:27]2[CH2:26][CH2:25][N:24]([C:18]3[CH:17]=[C:16]([O:15][CH3:14])[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=3)[CH2:29][CH2:28]2)[CH2:5][CH2:6]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27362051-(3,5-Dimethoxyphenyl)piperazineHCID 143302824-(2-bromoethyl)-3,4-dihydro-2H-benzopyran

Product 1

HCID 221542421-[2-(3,4-dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(3,5-dimethoxyphenyl)piperazine dihydrochloride

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 3776IsopropanolSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

The procedure of Example 1 is followed, starting 4-(2-bromoethyl)-3,4-dihydro(2H)-benzopyran (2 g), 1-(3,5-dimethoxyphenyl)piperazine (1.84 g) and dry potassium carbonate (0.56 g), followed by potassium iodide (1.4 g) in 2-butanone (70 cc). The residue obtained is chromatographed on a column 4.4 cm in diameter, containing silica gel (100 g), using a dichloromethane-ethyl acetate mixture (50-50 by volume) as eluent and collecting 20-cc fractions. The fractions between 200 and 400 cc are concentrated to dryness. The oil obtained is taken up with ethanol (30 cc) and a 5N solution of hydrochloric acid in isopropanol (1.8 cc) is added. The crystals formed are filtered off and 1-[2-(3,4-dihydro-1(2H)-benzopyran-4-yl)ethyl]-4-(3,5-dimethoxyphenyl)piperazine dihydrochloride (1.9 g) is thus obtained in the form of a solid melting at 208° C.

Workup

  1. customThe residue obtained
  2. customis chromatographed on a column 4.4 cm in diameter
  3. additioncontaining silica gel (100 g)
  4. customcollecting 20-cc fractions
  5. concentrationThe fractions between 200 and 400 cc are concentrated to dryness
  6. customThe oil obtained
  7. customThe crystals formed
  8. filtrationare filtered off

Sources & evidence

ORD record
ord-e82f65f8a53b40b6b01adf8df1dfabba
Source dataset
uspto-grants-1990_12
Patent number
US04977166

Reaction notes

Loading…