Phenethylamine → N-(2-phenylethyl) 1,2,3,4-tetrahydro-2-naphthoic amide

HRID 1720967Notes

Reaction equation

HRID 1720967 reaction equation
[CH2:1]([NH2:9])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH:11]1[C:20](Cl)=[O:21].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[C:3]1([CH2:2][CH2:1][NH:9][C:20]([CH:11]2[CH2:12][CH2:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:10]2)=[O:21])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 11430Potassium CarbonateHCID 156707901,2,3,4-Tetrahydronaphthalene-2-carbonyl chloride

Product 1

HCID 53953585N-(2-phenylethyl) 1,2,3,4-tetrahydro-2-naphthoic amideYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The solution of phenethylamine (344 mg, 2.84 mmol) in 20 ml of CH2Cl2 was first treated with the solution of 1,2,3,4-tetrahydro-2-naphthoyl chloride (2.83 mmol) in 2 ml of CH2Cl2 followed by treatment with 10 ml 10% K2CO3 solution. After stirred at r.t. overnight, the organic layer was separated and washed with 2N HCl, water, sat'd brine and dried over Na2SO4. Filtration and removal of solvent gave N-(2-phenylethyl) 1,2,3,4-tetrahydro-2-naphthoic amide as a white powder (793 mg, 100%); mp 86°-87° C.; Calcd for C19H21NO: C 81.67, H 7.59, N 5.01; Found: C 82.00, H 7.27, N 4.77.

Workup

  1. customthe organic layer was separated
  2. washwashed with 2N HCl, water
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and removal of solvent

Sources & evidence

ORD record
ord-518394860e824f49b43c3a05d79c4cb8
Source dataset
uspto-grants-1996_04
Patent number
US05508306

Reaction notes

Loading…