Pyridine → [2-(1H-Indol-3-yl)-1-methylethyl]carbamic acid phenyl ester

HRID 1394251Notes

Reaction equation

HRID 1394251 reaction equation
[C:1]1([O:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[NH:17]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:19]([CH2:26][CH:27]([NH2:29])[CH3:28])=[CH:18]1>C(Cl)Cl>[C:1]1([O:7][C:8](=[O:9])[NH:29][CH:27]([CH3:28])[CH2:26][C:19]2[C:20]3[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:17][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9287(+-)-alpha-MethyltryptamineHCID 15891Phenyl chloroformate

Product 1

HCID 69217046[2-(1H-Indol-3-yl)-1-methylethyl]carbamic acid phenyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroformic acid phenyl ester (760 μl, 6.03 mmole) and pyridine (510 μl, 6.31 mmole) were added to a solution of 2-(1H-indol-3-yl)-1-methyl-ethylamine (1.0 g, 5.74 mmole) in abs. DCM (20 ml). Stirring was then performed for 24 h at RT. Working up was performed by extracting the batch with water (2×20 ml), with 1M HCl (2×20 ml) and with 1M NaOH (2×20 ml). The organic phase was dried with Na2SO4 and evaporated. [2-(1H-Indol-3-yl)-1-methylethyl]carbamic acid phenyl ester was obtained as a colorless solid in a yield of 1.35 g (80%).

Workup

  1. extractionby extracting the batch with water (2×20 ml)
  2. dry with materialThe organic phase was dried with Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-6de003af59a141258ff77d7e6f841ab6
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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