Acetic Acid → 1-Naphthaleneethanamine, N,N-diethyl-

HRID 1440188Notes

Reaction equation

HRID 1440188 reaction equation
[C:1](O)(=O)[CH3:2].[CH2:5]([NH:7][CH2:8][CH3:9])[CH3:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>>[C:18]1([CH2:6][CH2:5][N:7]([CH2:1][CH3:2])[CH2:8][CH3:9])[C:17]2[C:16](=[CH:17][CH:18]=[CH:19][CH:16]=2)[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8021DiethylamineHCID 8058HexaneHCID 21226445Aluminium lithium hydride

Product 1

HCID 100366991-Naphthaleneethanamine, N,N-diethyl-

Procedure

The Pt catalyst solution used in these preparations was a solution of Karsted's catalyst in hexane. The solvents used were spectral grade, dried over molecular sieves. 1-(naphthyl)-2-(diethylamino) ethane was prepared according to methods outlined by Chandross and Thomas in Chem. Phys. Letters 9 393(1971). 1-napthylenyl acetic acid was converted to the acid chloride, reacted with diethylamine to make the corresponding amide and reduced to the corresponding amine using lithium aluminum hydride. Extraction from basic aqueous solution into ether gave the desired product in high yield.

Workup

  1. customdried over molecular sieves
  2. extractionExtraction from basic aqueous solution into ether

Sources & evidence

ORD record
ord-5e98a4ce0bac436caa9fb081f68634fb
Source dataset
uspto-grants-1996_03
Patent number
US05498549

Reaction notes

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