Hydrochloric Acid → HCID 19972701, compound

HRID 1452343Notes

Reaction equation

HRID 1452343 reaction equation
[CH:1]([C:3]1[C:12]2[O:11][C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:9]([CH3:19])[C:8](=[O:20])[C:7]=2[CH:6]=[CH:5][CH:4]=1)=O.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:34][CH2:33][N:32]([CH2:35][CH2:36][CH2:37][NH2:38])[CH2:31][CH2:30]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[ClH:53].[OH-].[Na+]>O.C(O)(=O)C.ClCCCl>[ClH:53].[ClH:53].[ClH:53].[CH3:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[N:29]1[CH2:30][CH2:31][N:32]([CH2:35][CH2:36][CH2:37][NH:38][CH2:1][C:3]2[C:12]3[O:11][C:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[C:9]([CH3:19])[C:8](=[O:20])[C:7]=3[CH:6]=[CH:5][CH:4]=2)[CH2:33][CH2:34]1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 104672591-(3-Aminopropyl)-4-(2-methoxyphenyl)piperazineHCID 19972556HCID 19972556, compound

Product 1

HCID 19972701HCID 19972701, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a mixture of 0.53 g of 8-formyl-3-methyl-4-oxo-2-phenyl-4H-1-benzopyran, 0.55 g of 3-[4-(2-methoxyphenyl)-1-piperazinyl]propylamine, 70 ml of 1,2-dichloroethane and 0.11 ml of acetic acid was added 0.64 g of sodium triacetoxyborohydride. The mixture was stirred at room temperature for 4.5 hours. The reaction mixture was poured into 100 ml of water and acidified with 37% hydrochloric acid. This was followed addition of cold 6N aqueous sodium hydroxide to make the solution alkaline. The mixture was extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous sodium sulfate. After evaporation of the solvent, (in vacuo) the residue was purified by flash chromatography on silica gel eluting with chloroform/methanol (100:5). The fractions containing the pure base were combined and the solvent was evaporated to dryness. The title compound, obtained as a base, was converted in the usual manner into the trihydrochloride salt, and crystallized from ethanol, m.p. 170°-176° C. (dec.).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter evaporation of the solvent, (in vacuo) the residue
  5. customwas purified by flash chromatography on silica gel eluting with chloroform/methanol (100:5)
  6. additionThe fractions containing the pure base
  7. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-9f240689ce9f4e758ff7c6ac99c79c83
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

Loading…