Water → 9-gamma-Aminopropyl-9,10-dihydro-9,10-methanoanthracene

HRID 27956Notes

Reaction equation

HRID 27956 reaction equation
[CH:1]1[C:14]2[C:13]3([CH2:16][CH2:17][C:18]#[N:19])[CH2:15][CH:6]([C:7]4[C:12]3=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCOCC1.C(OCC)(=O)C>[NH2:19][CH2:18][CH2:17][CH2:16][C:13]12[CH2:15][CH:6]([C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:14]=31)[C:7]1[C:12]2=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 962WaterHCID 15586334HCID 15586334, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 130690819-gamma-Aminopropyl-9,10-dihydro-9,10-methanoanthracene

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of β-(9,10-dihydro-9,10-methano-9-anthryl)propionitrile (250 mg) and lithium aluminum hydride (100 mg) in dioxane (12 ml) was stirred at 60° C. for 5 hours. Excess lithium aluminum hydride was decomposed by addition of water. The reaction mixture was diluted with ethyl acetate, dried over anhydrous sodium sulfate and evaporated to dryness to give 9-γ-aminopropyl-9,10-dihydro-9,10-methanoanthracene, which was converted into its hydrochloride. M.P. 275° C. (decomp.).

Workup

  1. dry with materialdried over anhydrous sodium sulfate
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-e2a72664756e4784aedd428941147c8c
Source dataset
uspto-grants-1980_09
Patent number
US04224344

Reaction notes

Loading…