Phenyl chloroformate → phenyl 2-(5-chloro-1H-indol-3-yl)ethylcarbamate

HRID 1918544Notes

Reaction equation

HRID 1918544 reaction equation
C(N(CC)C(C)C)(C)C.Cl.[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[CH2:21][CH2:22][NH2:23].Cl[C:25]([O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:26]>ClCCl>[Cl:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH:16]=[C:15]2[CH2:21][CH2:22][NH:23][C:25](=[O:26])[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 15891Phenyl chloroformateHCID 81531DiisopropylethylamineHCID 28274945-Chloro-1H-indole-3-ethylamine monohydrochloride

Product 1

HCID 66831882phenyl 2-(5-chloro-1H-indol-3-yl)ethylcarbamateYield 88.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N-diisopropylethylamine (0.745; 4.33 mmol) was added to a mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (0.500 g; 2.16 mmol), and phenyl chloroformate (0.406 mL; 3.25 mmol) in dichloromethane (20 mL). The solution was stirred at room temperature. for 20 minutes, diluted in dichloromethane, washed with sodium hydrogen sulfate (1M, water), sodium carbonate (1M, water) and brine. The organic layer was dried and concentrated under reduced pressure to furnish 0.60 g (88%) of phenyl 2-(5-chloro-1H-indol-3-yl)ethylcarbamate as a yellow oil.

Workup

  1. washwashed with sodium hydrogen sulfate (1M, water), sodium carbonate (1M, water) and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55121b087d9f42be8fa2a32a3897773d
Source dataset
uspto-grants-2013_12
Patent number
US08618138B2

Reaction notes

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