Diethyl Ether → 2-(Adamantan-2-yl)ethan-1-amine

HRID 461997Notes

Reaction equation

HRID 461997 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)C.[CH:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH:13]1[CH2:22][C:23]#[N:24])[CH2:19]2>O>[CH:12]12[CH2:21][CH:16]3[CH2:17][CH:18]([CH2:20][CH:14]([CH2:15]3)[CH:13]1[CH2:22][CH2:23][NH2:24])[CH2:19]2

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 12571472HCID 12571472, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 644112-(Adamantan-2-yl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.051 Mole of lithium aluminum hydride is dissolved in 200 ml. of anhydrous ethyl ether at 0° C, under nitrogen. 0.0571 Mole of adamant-2-yl acetonitrile in 100 ml. of anhydrous ethyl ether is added dropwise with stirring and the mixture is allowed to warm to room temperature and stirred for one hour. 10 Ml. of water is added dropwise and the mixture then filtered. The filtrate is dried over potassium hydroxide pellets and then filtered. The filtrate is distilled to remove the solvent affording 2-(adamant-2-yl)ethylamine.

Workup

  1. customat 0° C
  2. stirringstirred for one hour
  3. filtrationthe mixture then filtered
  4. dry with materialThe filtrate is dried over potassium hydroxide pellets
  5. filtrationfiltered
  6. distillationThe filtrate is distilled
  7. customto remove the solvent

Sources & evidence

ORD record
ord-4e6c68a254ed46c19719c17aa1e90ab4
Source dataset
uspto-grants-1977_12
Patent number
US04064258

Reaction notes

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