Phenethylamine → HCID 131719125, compound

HRID 2399824Notes

Reaction equation

HRID 2399824 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=1)([CH:8]1[CH2:12][CH2:11][CH2:10][CH2:9]1)[C:6]#[N:7].[CH2:20](CN)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:29][N:30](C)C=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[ClH:1].[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:5]([CH2:4][CH2:3][CH2:2][N:30]([CH3:29])[CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[C:6]#[N:7])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 1001PhenethylamineHCID 6228DimethylformamideHCID 21181695HCID 21181695, compound

Product 1

HCID 131719125HCID 131719125, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

The product from Example 4, Step (b) (1.99 g, 7.06 mmol) was combined with N-benzylmethylamine (1.82 mL, 14.1 mmol), N,N-dimethylformamide (3.5 mL) and tetrabutylammonium iodide (130 mg). The mixture was heated at 50° C. overnight, then diluted with water (25 mL) and extracted with ethyl acetate (100 mL, then 2×25 mL). The combined organic layers were dried over MgSO4, filtered through silica, concentrated and subjected to chromatography. The product was converted to the hydrochloride salt using hydrogen chloride gas in methylene chloride. The salt was recrystallized from dichloromethane/methyl acetate/hexane, affording the a product compound which was characterized as follows: 13C NMR of free base (CDCl3), 100 MHz, partial): 62.1, 56.5, 52.4, 50.1, 42.0, 37.2, 29.5, 29.2, 25.4, 24.8, 23.1; Analysis Cal'd. for C24H30ClFN2. 0.25 H2O: C, 71.09; H, 7.58; N, 6.91; Found: C, 70.92; H, 7.53; N, 6.84.

Workup

  1. extractionextracted with ethyl acetate (100 mL
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered through silica
  4. concentrationconcentrated
  5. customThe salt was recrystallized from dichloromethane/methyl acetate/hexane
  6. customaffording the a product compound which

Sources & evidence

ORD record
ord-1ec585206de449d0b1e9290b43197133
Source dataset
uspto-grants-1995_09
Patent number
US05451604

Reaction notes

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