* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
[(1-benzyl)piperidin-4-yl]-[1-(2-fluorobenzyl)-2-pyrryl]methanol[ No CAS ]
[ 63880-57-9 ]
[ 98460-37-8 ]
Yield
Reaction Conditions
Operation in experiment
With NaH; In N,N-dimethyl-formamide; benzene;
EXAMPLE 5 11-[(1-Benzyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine To a suspension of NaH (2.4 g, 0.05 mole, 50% in oil, treated with hexanes) in 20 ml dry benzene, was added a solution of [(1-benzyl)piperidin-4-yl]-[1-(2-fluorobenzyl)-2-pyrryl]methanol (15.0 g, 0.04 mole; prepared from 1-(2-fluorobenzyl)pyrrole-2-carboxaldehyde and <strong>[67848-71-9]1-benzyl-4-chloropiperidine</strong> in a manner substantially the same as described in Example 1) in 80 ml dry benzene followed by 25 ml DMF. After stirring at 80 C. for three hours, the mixture was poured into 200 ml iced water, stirred for ten minutes and then diluted with 100 ml ester. The organic layer was collected, washed twice with water and dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvents were evaporated to an oil, which solidified upon trituration with hexanes to 10.0 g (71%) of a solid, m.p. 111-113 C. This material was recrystallized twice from hexanes to yield a solid, m.p. 113-115 C. ANALYSIS: Calculated for C24 H26 N2 O: 80.41% C; 7.31% H; 7.82% N; Found: 80.56% C; 7.37% H; 7.79% N.
With NaH; In N,N-dimethyl-formamide; benzene;
EXAMPLE 5 11-[(1-Benzyl)piperidin-4-yl]-5H,11H-pyrrolo[2,1-c][1,4]benzoxazepine To a suspension of NaH (2.4 g, 0.05 mole, 50% in oil, treated with hexanes) in 20 ml dry benzene, was added a solution of [(1-benzyl)piperidin-4-yl]-[1-(2-fluorobenzyl)-2-pyrryl]methanol (15.0 g, 0.04 mole; prepared from 1-(2-fluorobenzyl)pyrrole-2-carboxaldehyde and <strong>[67848-71-9]1-benzyl-4-chloropiperidine</strong> in a manner substantially the same as described in Example 1) in 80 ml dry benzene followed by 25 ml DMF. After stirring at 80 C. for three hours, the mixture was poured into 200 ml iced water, stirred for ten minutes and then diluted with 100 ml ether. The organic layer was collected, washed twice with water and dried (saturated NaCl, anhydrous MgSO4). After filtering, the solvents were evaporated to an oil, which solidified upon trituration with hexanes to 10.0 g (71%) of a solid, m.p. 111-113 C. This material was recrystallized twice from hexanes to yield a solid, m.p. 113-115 C.
α-(1-Benzyl-4-piperidinyl)-1-[(2-fluorophenyl)phenylmethyl]-1H-pyrrole-2-methanol oxalate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With magnesium; In tetrahydrofuran; diethyl ether; ammonium chloride;
EXAMPLE 7 alpha-(1-Benzyl-4-piperidinyl)-1-[(2-fluorophenyl)phenylmethyl]-1H-pyrrole-2-methanol oxalate To magnesium turnings (1.51 g) in 30 ml of 10% Et2 O/THF was added a few drops of 1,2-dibromoethane, followed by a few drops of a solution of <strong>[67848-71-9]4-chloro-1-benzylpiperidine</strong> (13.0 g in 80 ml of 10% Et2 O/THF). The reaction mixture was heated and the rest of the <strong>[67848-71-9]4-chloro-1-benzylpiperidine</strong> solution was added slowly. The mixture was refluxed for three hours during which time it turned cloudy. The heat was removed and a solution of 1-[(2-fluorophenyl)phenylmethyl]pyrrole-2-carboxaldehyde 17.32 g in 150 ml of THF was slowly added. The solution cleared up a short time later and this mixture was stirred at reflux for 3 hours. The reaction was cooled and quenched in 400 ml of iced NH4 Cl solution. This was extracted with Et2 O (4*). The organics were washed with H2 O and dried with sat. NaCl and MgSO4. The mixture was filtered and the filtrate concentrated to an orange oil and the alcohol was separated via HPLC to yield 9.89 g of a pure yellow oil. A portion of this was made into the oxalate salt with ethereal oxalic acid yielding a slightly yellow solid which was recrystallized from isopropyl ether/ethanol to yield an analytically pure white solid, mp=yellows at 100 C.; decomposes at 130 C.). ANALYSIS: Calculated for C30 H31 FN2 O.C2 H2 O4: 70.57%C, 6.11%H, 5.14%N. Found: 70.69%C, 6.39%H, 4.75%N.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
Life Science
For Research Only
100K+ Compounds
Competitive Price
1-2 Day Shipping
