Methyl chloroformate → HCID 59831668, compound

HRID 268749Notes

Reaction equation

HRID 268749 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([CH:10]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][CH2:12][NH2:13])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl[C:21]([O:23][CH3:24])=[O:22]>C(Cl)Cl>[CH3:24][O:23][C:21](=[O:22])[NH:13][CH2:12][CH2:11][CH:10]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 25261580HCID 25261580, compound

Product 1

HCID 59831668HCID 59831668, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of 3-(1H-indol-4-yl)-3-phenyl-propylamine (III) (0.40 g, 1.6 mmol) in DCM (15 ml), under N2, was added TEA (0.23 ml, 1.7 mmol). The mixture was cooled to about 0° C. and methyl chloroformate (0.13 ml, 1.7 mmol) in DCM (10 ml) was added dropwise over 15 minutes. The mixture was stirred at room temperature for 30 minutes, quenched by addition of H2O, and stirred for 10 min. The mixture was washed successively with H2O and brine, dried over Na2SO4, filtered, and concentrated in vacuo to provide [3-(1H-indol-4-yl)-3-phenyl-propyl]-carbamic acid methylester (V) as a white solid (0.48 g, 98% yield).

Workup

  1. customquenched by addition of H2O
  2. stirringstirred for 10 min
  3. washThe mixture was washed successively with H2O and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c6ed860f74c749099383eb738808e059
Source dataset
uspto-grants-2008_11
Patent number
US07446118B2

Reaction notes

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