Sodium hydride → HCID 23284919, compound

HRID 369187Notes

Reaction equation

HRID 369187 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:34])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27](=[O:33])[CH2:28][CH2:29][CH2:30][CH2:31][Cl:32])[CH:21]=2)[CH2:15][CH2:14]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CN(C)C=O>[ClH:32].[CH3:3][N:4]([CH:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:34])[C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N:26]3[CH2:31][CH2:30][CH2:29][CH2:28][C:27]3=[O:33])[CH:21]=2)[CH2:15][CH2:14]1)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 23285148HCID 23285148, compound

Product 1

HCID 23284919HCID 23284919, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

230 mg of sodium hydride was added, under ice-cooling, to a solution of 2.2 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-[3-(5-chlorovalerylamino)benzoyl]piperidine in 20 ml of dimethylformamide. The mixture was stirred at the same temperature for 30 minutes. The reaction mixture was poured into ice water. The mixture was extracted with methylene chloride. The extract was washed with a saturated aqueous sodium chloride solution, dried with magnesium sulfate, and concentrated under reduced pressure. The residue was purified by a silica gel column chromatography (eluant: methylene chloride/methanol=100/3 to 20/1) and then converted into a hydrochloride. The hydrochloride was solidified from ethanol-diethyl ether to obtain 1.7 g of 4-[N-methyl-N-(2-phenylethyl)amino]-1-[3-(2-oxo-1-piperidinyl)benzoyl]piperidine hydrochloride as a white amorphous.

Workup

  1. extractionThe mixture was extracted with methylene chloride
  2. washThe extract was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by a silica gel column chromatography (eluant: methylene chloride/methanol=100/3 to 20/1)

Sources & evidence

ORD record
ord-68fffd9172974af498f5fe46b2b4e859
Source dataset
uspto-grants-2000_10
Patent number
US06136826

Reaction notes

Loading…