Diphenylacetaldehyde → 1-(2,2-Diphenylethyl)-4-[4-(methylsulfonyl)benzyl]homopiperazine

HRID 2119350Notes

Reaction equation

HRID 2119350 reaction equation
[CH3:1][S:2]([C:5]1[CH:18]=[CH:17][C:8]([CH2:9][N:10]2[CH2:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:19]1([CH:25]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=O)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[C:19]1([CH:25]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:26][N:13]2[CH2:14][CH2:15][CH2:16][N:10]([CH2:9][C:8]3[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:18][CH:17]=3)[CH2:11][CH2:12]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 13696DiphenylacetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 234410231-[4-(Methylsulfonyl)benzyl]homopiperazine

Product 1

HCID 234410381-(2,2-Diphenylethyl)-4-[4-(methylsulfonyl)benzyl]homopiperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The resulting 1-[4-(methylsulfonyl)benzyl]homopiperazine was dissolved in 5 mL of dichloromethane, followed by adding 223 mg of diphenylacetaldehyde and 217 mg of sodium triacetoxyborohydride. After the mixture was stirred at room temperature for 16 hours, it was mixed with 30 mL of aqueous saturated sodium hydrogencarbonate, and extracted with 30 mL×2 of ethyl acetate. The organic layers were combined, washed with 30 mL of saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography (silica gel, ethyl acetate) to obtain 173 mg of the titled compound. This was treated with a hydrogen chloride solution in ether and the solvent was removed under reduced pressure, the residue was dried to give the hydrochloride salt of the titled compound.

Workup

  1. extractionextracted with 30 mL×2 of ethyl acetate
  2. washwashed with 30 mL of saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-a43464fbfd114b63b1cb40b8ed2cb2e1
Source dataset
uspto-grants-2004_02
Patent number
US06686353B1

Reaction notes

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