HCID 10759534, compound → 1-Benzyl-4-(N-methyl-N-(3-hydroxymethyl-2-pyridyl)amino)piperidine

HRID 361804Notes

Reaction equation

HRID 361804 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[C:20]([C:21](OC)=[O:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:25])[C:15]2[C:20]([CH2:21][OH:22])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10759534HCID 10759534, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 106387941-Benzyl-4-(N-methyl-N-(3-hydroxymethyl-2-pyridyl)amino)piperidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a flame-dried flask containing 1-benzyl-4-(N-methyl-N-(3-methoxycarbonyl-2-pyridyl)amino)piperidine (XXIX, EXAMPLE 34, 750 mg) in dry tetrahydrofuran (22 ml) at 0° under nitrogen is added lithium aluminum hydride (84 mg) in two portions. The mixture is stirred at 0° for 1.5 hrs, quenched carefully with aqueous sodium hydroxide (5%, 5 ml), diluted with water (10 ml) and filtered through a pad of diatomaceous earth. The filtrate is then extracted with methylene chloride (2×30 ml) and the combined organic phases are washed with saline (10 ml), dried over sodium sulfate and concentrated under reduced pressure to give the title compound, NMR (CDCl3, 400 MHz) 8.28, 7.53, 7.31, 7.24, 6.99, 4.90, 4.71, 3.48, 3.16, 2.91, 2.74, 1.99 and 1.74δ.

Workup

  1. customquenched carefully with aqueous sodium hydroxide (5%, 5 ml)
  2. additiondiluted with water (10 ml)
  3. filtrationfiltered through a pad of diatomaceous earth
  4. extractionThe filtrate is then extracted with methylene chloride (2×30 ml)
  5. washthe combined organic phases are washed with saline (10 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0662be75139a40bdb921ded97bae0e09
Source dataset
uspto-grants-1999_02
Patent number
US05866589

Reaction notes

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