Chloroform → HCID 53693471, compound

HRID 1978021Notes

Reaction equation

HRID 1978021 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C@H:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6]1.C(N(CC)CC)C.[CH2:23]([N:25]=[C:26]=[O:27])[CH3:24].C(Cl)(Cl)Cl>C(#N)C.O>[CH2:23]([NH:25][C:26](=[O:27])[NH:2][CH2:3][CH2:4][C@H:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([O:14][CH3:15])[CH:12]=2)[CH2:7][CH2:6]1)[CH3:24]

Participants

7

Reactant 4

HCID 6212ChloroformHCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 70237232HCID 70237232, compound

Product 1

HCID 53693471HCID 53693471, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a suspension of (S)-1-(2-aminoethyl)-6-methoxyindan hydrochloride (0.10 g, 0.44 mmol) and triethylamine (61 μl, 0.44 mmol) in acetonitrile (3 ml) was added ethyl isocyanate (35 μl, 0.44 mmol). The mixture was stirred for 30 min at room temperature, then diluted with water and the product was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and brine, dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. The residue was recrystallized from ethyl acetate and isopropyl ether to afford the titled compound (79 mg, yield 69%), m.p. 104-105° C. [α]Hg365 +48.80 (c 0.5, CHCl3)

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe extract was washed with 1N hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. customThe residue was recrystallized from ethyl acetate and isopropyl ether

Sources & evidence

ORD record
ord-7835e11ae5bf4bf4ae1ded50c8edfad6
Source dataset
uspto-grants-2001_05
Patent number
US06235789B1

Reaction notes

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