Sodium Hydroxide → HCID 21081062, compound

HRID 1965946Notes

Reaction equation

HRID 1965946 reaction equation
[OH:1][CH:2]1[C:7]2([C:12](=O)[NH:11][CH2:10][CH2:9][CH2:8]2)[CH2:6][N:5]([CH3:14])[CH2:4][CH2:3]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[H][H].[OH-].[Na+]>O1CCCC1.O>[CH3:14][N:5]1[CH2:4][CH2:3][CH:2]([OH:1])[C:7]2([CH2:8][CH2:9][CH2:10][NH:11][CH2:12]2)[CH2:6]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21080316HCID 21080316, compoundHCID 21226445Aluminium lithium hydrideHCID 178418361HCID 178418361, compound

Product 1

HCID 21081062HCID 21081062, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Of the 11-hydroxy-8-methyl-2,8-diaza-spiro[5.5]undecan-1-one obtained, 2 g are taken up in 20 ml of absolute tetrahydrofuran; this solution is added dropwise, with stirring, to 1 g of LiAlH4 in 50 ml of absolute tetrahydrofuran. The temperature rises to 36° C., while hydrogen is given off in copious amounts. After another 3 hours at ambient temperature the mixture is refluxed for 10 hours. The reaction is stopped by the addition of 2 ml of water and 2 ml 1N aqueous sodium hydroxide solution while cooling with ice. The product is extracted with ethyl acetate and the solvent is eliminated in vacuo. Then the amine is precipitated from absolute ethanol with HCl gas, in the form of the hydrochloride. Yield 1.44 g.

Workup

  1. additionthis solution is added dropwise
  2. temperaturewhile cooling with ice
  3. extractionThe product is extracted with ethyl acetate
  4. customThen the amine is precipitated from absolute ethanol with HCl gas, in the form of the hydrochloride

Sources & evidence

ORD record
ord-e275df66716f49c3a9ea28b54626b970
Source dataset
uspto-grants-2013_04
Patent number
US08420630B2

Reaction notes

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