Water → HCID 19772039, compound

HRID 1614601Notes

Reaction equation

HRID 1614601 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:18]2[CH2:23][CH2:22][N:21]([S:24]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH2:20][CH2:19]2)=[N:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].O>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:18]2[CH2:19][CH2:20][N:21]([S:24]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)(=[O:25])=[O:26])[CH2:22][CH2:23]2)[NH:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 19771928HCID 19771928, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19772039HCID 19772039, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10.0 g (0.022 mol) of α-(4-fluorophenyl)-N-(2-phenylethyl)-1-(phenylsulfonyl)-4-piperidinemethanimine and 1.0 g (0.025 mol) of LiAlH4 in 200 mL of dry THF was stirred at room temperature for 8.5 hr. A 10 mL solution of 10% NaOH was slowly added followed by 100 mL of water. The mixture was extracted with CH2Cl2, and the solution was dried (MgSO4). The solvent was removed in vacuo to give an oil. This was crystallized from 200 ml of methanol to give 7.32 g (72.9%) of a white crystalline solid, mp 115°-117° C.

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. dry with materialthe solution was dried (MgSO4)
  3. customThe solvent was removed in vacuo
  4. customto give an oil
  5. customThis was crystallized from 200 ml of methanol

Sources & evidence

ORD record
ord-ea42900c9e824dc399bfe247e4812ea0
Source dataset
uspto-grants-1993_03
Patent number
US05198449

Reaction notes

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