Phenethylamine → HCID 22022378, compound

HRID 1793489Notes

Reaction equation

HRID 1793489 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[C:7]1([CH2:13][CH2:14][NH2:15])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[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]CCl>CS(C)=O.O>[C:7]1([CH2:13][CH2:14][NH:15][CH2:1][CH:27]([O:26][C:17]2[CH:18]=[CH:19][C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH:16]=2)[CH2:28][CH3:29])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 11430Potassium CarbonateHCID 116587114-(2-Naphthyloxy)-1-chlorobutane

Product 1

HCID 22022378HCID 22022378, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of anhydrous potassium carbonate (10 gm, in excess) and phenylethylamine (0.4 ml, 0.003 mole) was taken in dry DMSO (40 ml). Now 4-(2-naphthyloxy)-1-chlorobutane (0.5 gm, 0.002 mole) was added in it. Reaction mixture was refluxed at 140° C. for 8 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 oily compound which was later crystallized by benzene hexane to get N-(2-phenylethyl)-(2-(naphthalen-2-yloxy)butyl)amine, solid, m.p. 139° C., (yield 0.656 gm, 95.6%).

Workup

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

Sources & evidence

ORD record
ord-d1a84167fdfa4a05958f2dc9d7eb359b
Source dataset
uspto-grants-2006_07
Patent number
US07081465B2

Reaction notes

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