Phenethylamine → HCID 21181135, compound

HRID 2399825Notes

Reaction equation

HRID 2399825 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([CH:17]([CH3:19])[CH3:18])([C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=1)[C:8]#[N:9].[CH2:20](CN)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[CH3:29][N:30](C)C=O.C(N(C(C)C)CC)(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[F:16][C:13]1[CH:14]=[CH:15][C:10]([C:7]([CH:17]([CH3:19])[CH3:18])([CH2:6][CH2:5][CH:4]([N:30]([CH3:29])[CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:3][CH3:2])[C:8]#[N:9])=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 1001PhenethylamineHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 21181059HCID 21181059, compound

Product 1

HCID 21181135HCID 21181135, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

The product from Example 6, Step (a) (0,538 g, 1.91 mmol) was combined with N-benzylmethylamine (0.28 mL, 2.2 mmol), N,N-dimethylformamide (1.3 mL), diisopropylethylamine (0.33 mL, 1.91 mmol), and tetrabutylammonium iodide, and the mixture was then stirred at 70° C. overnight. Upon cooling, the reaction product was diluted with ethyl acetate (50mL) and washed with half-saturated sodium bicarbonate (30 mL). The aqueous layer was extracted with additional ethyl acetate (2×30 mL). The combined organic was dried over MgSO4, and the crude product was concentrated. Silica gel chromatography, using diethyl ether as the eluent, followed by concentration, afforded a product compound as an oil which was characterized by NMR as follows: NMR (free base) (CDCl3, 400 MHz, partial): 3.91 (s, 2H); 2.13 (s, 3H); 1.18 (d, 3H, J=6 Hz); 0.75 (d, 3H, J=6 Hz); Analysis calc'd. for C24H31FN2 : C, 78.64; H, 8.53; N, 7.64; Found: C, 78.54; H, 8.52; N, 7.84

Workup

  1. temperatureUpon cooling
  2. washwashed with half-saturated sodium bicarbonate (30 mL)
  3. extractionThe aqueous layer was extracted with additional ethyl acetate (2×30 mL)
  4. dry with materialThe combined organic was dried over MgSO4
  5. concentrationthe crude product was concentrated
  6. concentrationfollowed by concentration
  7. customafforded a product compound as an oil which

Sources & evidence

ORD record
ord-d56eaeee8981447e9d3176fee9c2bad6
Source dataset
uspto-grants-1995_09
Patent number
US05451604

Reaction notes

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