Ammonium Chloride → 1-(Diphenylmethyl)-4-[(2-phenyl-4-methylfuran-5-yl)eth-1-yl]piperazine

HRID 22263

Reaction equation

HRID 22263 reaction equation
[C:1]1([C:7]2[O:8][C:9]([CH:13]=O)=[C:10]([CH3:12])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]1([CH:21]([N:28]2[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[CH3:34][Mg]I.[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>O.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(Cl)Cl.C(OCC)C>[C:15]1([CH:21]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:28]2[CH2:29][CH2:30][N:31]([CH2:34][CH2:13][C:9]3[O:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)=[CH:11][C:10]=3[CH3:12])[CH2:32][CH2:33]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

10

Reactant 5

HCID 25517Ammonium ChlorideHCID 70048BenzhydrylpiperazineHCID 516892Sodium BicarbonateHCID 194302672-Phenyl-4-methyl-5-formylfuranHCID 178418373HCID 178418373, compound

Product 1

HCID 542165821-(Diphenylmethyl)-4-[(2-phenyl-4-methylfuran-5-yl)eth-1-yl]piperazine

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-phenyl-4-methyl-5-formylfuran (1.1 g), diphenylmethylpiperazine (1.5 g), and titanium(IV) isopropoxide (1.76 g) was stirred for 11/4 hours. Diethyl ether (20 ml) was added, and the resultant solution was stirred for 30 minutes. Methyl magnesium iodide (6 ml of 3M in ether) was then added dropwise, and the mixture stirred at room temperature for 1 hour. Ammonium chloride (20 ml of a saturated solution in water) was then added, followed by 300 ml of methylene chloride, and the mixture made basic with a solution of sodium bicarbonate. The residue was partitioned between methylene chloride/water, the organic layer separated, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel, eluting with 15% ethyl acetate in heptane with a trace of ammonia, to yield 0.51 g of 1-(diphenylmethyl)-4-[(2-phenyl-4-methylfuran-5-yl)eth-1-yl]piperazine. Treatment with anhydrous hydrochloric acid in ethanol converted the base to its dihydrochloride salt, m.p. 205°-208° C.

Workup

  1. customThe residue was partitioned between methylene chloride/water
  2. customthe organic layer separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was flash-chromatographed on silica gel
  7. washeluting with 15% ethyl acetate in heptane with a trace of ammonia

Sources & evidence

ORD record
ord-9c8de45512cf42c6925872739c3f6448
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Linked notes

Loading…