Water → 8-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-methanamine

HRID 67687Notes

Reaction equation

HRID 67687 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:9]1([N:19]([CH3:21])[CH3:20])[CH2:18][CH2:17][C:12]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:11][CH2:10]1)#[N:8].O.[OH-].[Na+]>C(OCC)C>[CH3:20][N:19]([CH3:21])[C:9]1([CH2:7][NH2:8])[CH2:18][CH2:17][C:12]2([O:13][CH2:14][CH2:15][O:16]2)[CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 3609778-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 205276208-(Dimethylamino)-1,4-dioxaspiro[4.5]decane-8-methanamine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 0.4 g portion of lithium aluminum hydride (LAH) is cooled in 10 ml of diethyl ether under nitrogen atmosphere. Then 2.0 g of 8-cyano-[1,4-dioxaspiro[4.5]dec-8-yl]dimethylamine (U.S. Pat. No. 4,065,573, Example 41, part B) was added over 20 minutes while stirring at room temperature. Then, in turn, there was added 0.4 ml of water, 0.4 ml of 15 percent sodium hydroxide and 1.2 ml of water. The inorganic gel in the mixture was filtered off. The filtrate was dried by evaporation under vacuum. A thin layer chromatography (tlc) sample analysis showed the residue to be largely one spot material. The Nuclear Magnetic Resonance spectrum (NMR) for this material was very good for the above-named chemical intermediate.

Workup

  1. addition4,065,573, Example 41, part B) was added over 20 minutes
  2. filtrationThe inorganic gel in the mixture was filtered off
  3. customThe filtrate was dried by evaporation under vacuum

Sources & evidence

ORD record
ord-1f9323f860a1473092bc4015766e1ed1
Source dataset
uspto-grants-1982_08
Patent number
US04346101

Reaction notes

Loading…