1'-benzylspiro[indoline-3,4'-piperidine]

Preparation of intermediate compound 15; CF3COOH (16.8 ml; 5 eq) was added at room temperature to a solution of phenylhydrazine (3.2 ml; 1.1 eq) in toluene/CH3CN (49/1) (50 ml). The mixture was heated at 35 °C. A solution of 1-(phenylmethyl)-4-piperidinecarboxaldehyde (6 g; 0.03 mol) in toluene/CH3CN (49/1) (10 ml) was added slowly. The mixture was heated at 35 °C overnight, then cooled down to -10 °C. Methanol (7 ml) was added then NaBH4 (1.7 g; 1.5 eq) was added portionwise. The mixture was stirred at room temperature for 1 hour. NH40H 10 percent was added, the mixture was extracted with EtOAc, dried over MgS04, filtered and evaporated. The residue (10 g) was purified by column chromatography over silica gel (75 g Si02 35-70 μm; eluent : 98/2 CH2Cl2/MeOH). Yield: 3.3 g of intermediate compound 15 (40 percent)Example AS; a. Preparation of intermediate compound 15; CF3COOH (16.8 ml; 5 eq) was added at room temperature to a solution of phenylhydrazine (3.2 ml; 1.1 eq) in toluene/CH3CN (49/1) (50 ml). The mixture was heated at 35 °C. A solution of 1-(phenylmethyl)-4-piperidinecarboxaldehyde (6 g; 0.03 mol) in toluene/CH3CN (49/1) (10 ml) was added slowly. The mixture was heated at 35 °C overnight, then cooled down to -10 °C. Methanol (7 ml) was added then NaBH4 (1.7 g; 1.5 eq) was added portionwise. The mixture was stirred at room temperature for 1 hour. NH40H 10 percent was added, the mixture was extracted with EtOAc, dried over MgS04, filtered and evaporated. The residue (10 g) was purified by column chromatography over silica gel (75 g Si02 35-70 μm; eluent : 98/2 CH2Cl2/MeOH). Yield: 3.3 g of intermediate compound 15 (40 percent)

Molecular Weight:278.4
XLogP3:3.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:278.178298710
Monoisotopic Mass:278.178298710
Topological Polar Surface Area:15.3
Heavy Atom Count:21
Complexity:340
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes