Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Benzyl Alcohol | HCID 244 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | HCID 23359068 | HCID 23359068 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 23359081 | HCID 23359081 | 93.6% |
Reaction Steps
A solution of 0.4 g of benzyl alcohol in 2 ml of dimethylformamide was dropwise added to a suspension of 150 mg of sodium hydride in 5 ml of dimethylformamide with ice-cooling. The mixture was stirred at the same temperature for 30 minutes. Thereto was dropwise added 1.0 g of 4-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinyl)carbonyl-2-chloroquinoline in 2 ml of dimethylformamide. The mixture was stirred at room temperature for 1 hour to give rise to a reaction. The reaction mixture was poured into ice water, followed by extraction with methylene chloride. The extract was washed with water and an aqueous sodium chloride solution in this order, then dried with magnesium sulfate and concentrated under reduced pressure to obtain 1.1 g of 4-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinyl)carbonyl-2-benzyloxyquinoline.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05591751 |
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| Source dataset | uspto-grants-1997_01 |
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| ORD ID | ord-22a495156dc142b8b32d429f10f95678 |
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| Source note | uspto-grants-1997_01 |
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