Tetrahydrofuran → N-(1-methyl-3-piperidinylmethyl)-N-cyclooctylmethylamine

HRID 483845Notes

Reaction equation

HRID 483845 reaction equation
O1CCCC1.[CH3:6][N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([C:13]([NH:15][CH2:16][CH:17]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)=O)[CH2:8]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>CO>[CH3:6][N:7]1[CH2:12][CH2:11][CH2:10][CH:9]([CH2:13][NH:15][CH2:16][CH:17]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:8]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 200816741-Methyl-3-cyclooctylmethylaminocarbonylpiperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 14747665N-(1-methyl-3-piperidinylmethyl)-N-cyclooctylmethylamineYield 85.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 50 ml of distilled tetrahydrofuran were added 3.2 g of 1-methyl-3-cyclooctylmethylaminocarbonylpiperidine and 1.5 g of lithium aluminum hydride. The mixture was refluxed for 10 hours under a nitrogen current. After cooling, the reaction mixture was mixed with methanol and 2N sodium hydroxide. The resulting mixture was stirred and then the insoluble materials were removed by filtration. The filtrate was concentrated. The residue was distilled in a glass tube over under reduced pressure to obtain 2.6 g of N-(1-methyl-3-piperidinylmethyl)-N-cyclooctylmethylamine.

Workup

  1. temperatureThe mixture was refluxed for 10 hours under a nitrogen current
  2. temperatureAfter cooling
  3. customthe insoluble materials were removed by filtration
  4. concentrationThe filtrate was concentrated
  5. distillationThe residue was distilled in a glass tube over under reduced pressure

Sources & evidence

ORD record
ord-5218164b65c84f2a9ffadfc53496820f
Source dataset
uspto-grants-1993_07
Patent number
US05227381

Reaction notes

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