Propargylamine → HCID 178456886, compound

HRID 1620579Notes

Reaction equation

HRID 1620579 reaction equation
[NH2:1][C:2]1=[N:3][C:4](=[O:30])[N:5]([CH3:29])/[C:6]/1=[CH:7]\[CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:16]=2[C:25]([F:28])([F:27])[F:26])[CH2:10][CH2:9]1.[CH2:31](N)[C:32]#[CH:33]>C1(C)C=CC=CC=1>[F:27][C:25]([F:26])([F:28])[C:16]1[CH:17]=[C:18]([C:21]([F:22])([F:23])[F:24])[CH:19]=[CH:20][C:15]=1[CH2:14][N:11]1[CH2:12][CH2:13][CH:8](/[CH:7]=[C:6]2/[C:2]([NH:1][CH2:33][C:32]#[CH:31])=[N:3][C:4](=[O:30])[N:5]/2[CH3:29])[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 239041PropargylamineHCID 86678753HCID 86678753, compound

Product 1

HCID 178456886HCID 178456886, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (5Z)-4-amino-5-({1-[2,4-bis(trifluoromethyl)benzyl]piperidin-4-yl}methylidene)-1-methyl-1,5-dihydro-2H-imidazol-2-one (1.50 g) in toluene (10 mL) was added propargylamine (1.90 g) at room temperature. The reaction mixture was stirred at 100° C. overnight. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) and recrystallized from ethyl acetate/heptane to give the title compound (870 mg).

Workup

  1. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  2. customrecrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-f9b2b331628e40f39d8fb97fe7327686
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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