Ethyl isocyanate → HCID 66792765, compound

HRID 534975Notes

Reaction equation

HRID 534975 reaction equation
Cl.Cl.[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:18][CH2:17][N:16]([C:19](=[O:29])[C:20]([NH:22][CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:21])[CH2:15][CH2:14]1)([CH3:6])([CH3:5])[CH3:4].[N:30]([CH2:33][CH3:34])=[C:31]=[O:32].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>O1CCCC1>[C:3]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[CH2:14][CH2:15][N:16]([C:19](=[O:29])[C:20]([NH:22][CH:23]2[CH2:24][CH2:25][N:26]([C:31]([NH:30][CH2:33][CH3:34])=[O:32])[CH2:27][CH2:28]2)=[O:21])[CH2:17][CH2:18]1)([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 66751186HCID 66751186, compound

Product 1

HCID 66792765HCID 66792765, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxo-N-piperidin-4-ylacetamide dihydrochloride (0.35 g, 0.79 mmol), isocyanatoethane (72.5 mg, 1.02 mmol) and triethylamine (329 μL, 2.36 mmol) in tetrahydrofuran (10 mL) was stirred at room temperature for 16 h. The reaction mixture was poured into saturated NaHCO3 solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound (0.34 g, 99%) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-682aaa98b5244bd786deb65df27a031e
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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