Benzyl Alcohol → HCID 23359081, compound

HRID 232701Notes

Reaction equation

HRID 232701 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:11][N:12]([CH:21]1[CH2:26][CH2:25][N:24]([C:27]([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=[C:31](Cl)[CH:30]=2)=[O:28])[CH2:23][CH2:22]1)[CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH3:11][N:12]([CH:21]1[CH2:26][CH2:25][N:24]([C:27]([C:29]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[N:32]=[C:31]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:30]=2)=[O:28])[CH2:23][CH2:22]1)[CH2:13][CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 23359068HCID 23359068, compound

Product 1

HCID 23359081HCID 23359081, compoundYield 93.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

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.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 1 hour
  3. customto give rise
  4. customto a reaction
  5. extractionfollowed by extraction with methylene chloride
  6. washThe extract was washed with water
  7. dry with materialan aqueous sodium chloride solution in this order, then dried with magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-22a495156dc142b8b32d429f10f95678
Source dataset
uspto-grants-1997_01
Patent number
US05591751

Reaction notes

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