Phenethylamine → HCID 131719125, compound

HRID 1386514Notes

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

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

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

Sources & evidence

ORD record: ord-831dc8c824fb43b684e6fef75ee49cf6
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265439B1

Reaction notes

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