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2-Ethylhexylamine → N-(2-ethyl-n-hexyl)-(3-(naphthalen-2-yloxy) propyl)amine

HRID 1793475
Notes
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Reaction equation

HRID 1793475 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7]([CH:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][NH2:11])[CH3:8].[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1[O:26][CH2:27][CH2:28][CH2:29]Cl>CS(C)=O.O>[CH2:7]([CH:9]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:10][NH:11][CH2:29][CH2:28][CH2:27][O:26][C:17]1[CH:18]=[CH:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:16]=1)[CH3:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 77192-EthylhexylamineHCID 11430Potassium CarbonateHCID 116872053-(2-Naphthyloxy)-1-chloropropane

Product 1

HCID 9995735N-(2-ethyl-n-hexyl)-(3-(naphthalen-2-yloxy) propyl)amine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962
Water
Solvent

Conditions

Temperature
140 °C

Procedure

A mixture of anhydrous potassium carbonate (10 gm, in excess) and 2-ethyl-n-hexylamine (0.35 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 3-(2-naphthyloxy)-1-chloropropane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 7 hrs and the reaction was completed as checked by TLC. Reaction mixture was poured in distilled water (60 ml) and extracted with ethyl acetate thrice. The organic layer was separated and concentrated to get oily compound which was later crystallized by benzene hexane to get N-(2-ethyl-n-hexyl)-(3-(naphthalen-2-yloxy) propyl)amine solid, m.p. 97° C., (yield 0.6 gm, 84.8%).

Workup

  1. customReaction mixture
  2. customReaction mixture
  3. extractionextracted with ethyl acetate thrice
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customto get oily compound which
  7. customwas later crystallized by benzene hexane

Sources & evidence

ORD record
ord-8791a47137a4489b86340d1a667d0da7
Source dataset
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07081465B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes