HCID 15291737, compound → HCID 22097496, compound

HRID 1734562Notes

Reaction equation

HRID 1734562 reaction equation
[C:1]([NH:4][CH2:5][C:6]1([OH:13])[CH2:11][CH2:10][N:9]([CH3:12])[CH2:8][CH2:7]1)(=O)[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:1]([NH:4][CH2:5][C:6]1([OH:13])[CH2:7][CH2:8][N:9]([CH3:12])[CH2:10][CH2:11]1)[CH3:2]

Participants

4

Reactant 2

HCID 15291737HCID 15291737, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 22097496HCID 22097496, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-acetamidomethyl-4-hydroxy-1-methylpiperidine (3.4 g, 0.018 mole) in dry THF was refluxed in the presence of lithium aluminium hydride (4 g). After 3 days, the mixture was poured into an ice-water bath and filtered through Celite. The solvent was evaporated and after addition of water the solution was extracted with chloroform, and the extract was dried with magnesium sulfate and evaporated to yield 1.03 g (33% yield) crude material. The product thus obtained, 4-ethylaminomethyl-4-hydroxy-1-methylpiperidine, was used without further purification.

Workup

  1. additionthe mixture was poured into an ice-water bath
  2. filtrationfiltered through Celite
  3. customThe solvent was evaporated
  4. additionafter addition of water the solution
  5. extractionwas extracted with chloroform
  6. dry with materialthe extract was dried with magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-2d6027d7969240d5817e7faf13742d29
Source dataset
uspto-grants-1996_07
Patent number
US05534520

Reaction notes

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