Triethylamine → 4-Fluoro-alpha-(2-[2-(2-naphthalenyl)ethylamino]ethyl)benzenemethanamine Dihydrochloride

HRID 2248407Notes

Reaction equation

HRID 2248407 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=O.C([N:15](CC)CC)C.[ClH:20].[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[CH2:31][CH2:32][NH2:33]>C1COCC1>[ClH:1].[ClH:20].[F:12][C:9]1[CH:10]=[CH:11][C:6]([CH:4]([CH2:3][CH2:2][NH:33][CH2:32][CH2:31][C:22]2[CH:23]=[CH:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=2)[NH2:15])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 676722-Chloro-4'-fluoropropiophenoneHCID 162181222-(Naphthalen-2-yl)ethan-1-amine hydrochloride

Product 1

HCID 199961454-Fluoro-alpha-(2-[2-(2-naphthalenyl)ethylamino]ethyl)benzenemethanamine Dihydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-chloro-4'-fluoropropiophenone (9.3 g, 0.05 mole) in 100 ml THF was treated with triethylamine (5.6 g, 0.055 mole) and stirred at room temperature for one hour. The mixture was treated with 2-naphthaleneethylamine hydrochloride (10.4 g, 0.05 mole) and refluxed for six hours. The reaction mixture was cooled to room temperature, and the resulting crystals were collected by filtration, washed with THF, ether, and water; and dried to give the title compound as a homogeneous product by tlc (chloroform-methanol, 9:1) (96%, 17.2 g); mp 208°-210° C.; IR(nujol): C=O @ 1675 cm-1 ; NMR(DMSO-d6, TMS): δ 3.20(t,2H, CH2 --CO), 3.37(m,4H,Ar--CH2 --CH2), 3.60(t,2H,N--CH2) [7.3-7.6(m,5H), 7.7-7.8(m,2H), 8.10(m,2H) aromatic]; Anal. Found: C,70.37; H,5.92; N,3.81. Mass spectrum m/e 321,184.

Workup

  1. temperaturerefluxed for six hours
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationthe resulting crystals were collected by filtration
  4. washwashed with THF, ether, and water
  5. customand dried

Sources & evidence

ORD record
ord-b8e07242d60149519281ecaf6939d085
Source dataset
uspto-grants-1991_08
Patent number
US05039706

Reaction notes

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