Water → HCID 19390916, compound

HRID 487175Notes

Reaction equation

HRID 487175 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][C:22](=[O:34])[C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[CH2:16][CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O>O1CCCC1>[CH2:7]([N:14]1[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][CH:22]([OH:34])[C:23]2[CH:28]=[CH:27][C:26]([N:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)=[CH:25][CH:24]=2)[CH2:18][CH2:19]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10090964HCID 10090964, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19390916HCID 19390916, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (10 mi) of 0.6 g of lithium aluminum hydride (0.6 g) in tetrahydrofuran was added 0.6 g of the 1-benzyl-4-[2-(4-pyrrolidinobenzoyl)ethyl]piperidine synthesized in Example 59 and the mixture was stirred at room temperature for 30 minutes. Then, water was added cautiously thereto for decomposing the excess reagent and the reaction product was then extracted into dichloromethane. The extract was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to give crude crystals. Recrystallization from ether-hexane yielded 0.5 g of colorless crystals melting at 93°-95° C.

Workup

  1. extractionthe reaction product was then extracted into dichloromethane
  2. dry with materialThe extract was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customto give crude crystals
  5. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-daf89626a2fa44bba597db956eee5f79
Source dataset
uspto-grants-1994_03
Patent number
US05294625

Reaction notes

Loading…