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

HRID 1654612Notes

Reaction equation

HRID 1654612 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 convened 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-bf99edfbd86c43d18b080111681d4ba4
Source dataset
uspto-grants-1995_04
Patent number
US05409666

Reaction notes

Loading…