Pyridine → HCID 60628064, compound

HRID 1394275Notes

Reaction equation

HRID 1394275 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.[NH2:17][CH2:18][CH2:19][C:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[NH:22][CH:21]=1>C(Cl)Cl>[C:1]1([O:7][C:8](=[O:9])[NH:17][CH2:18][CH2:19][C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 1150TryptamineHCID 15891Phenyl chloroformate

Product 1

HCID 60628064HCID 60628064, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroformic acid phenyl ester (3.29 g, 21.0 mmole) and pyridine (1.74 g, 22.0 mmole) were added to a solution of tryptamine (3.2 g, 20.0 mmole) in abs. DCM (50 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 1M NaOH (2×20 ml). The organic phase was dried with Na2SO4 and then evaporated. [2-(1H-Indol-3-yl)ethyl]carbamic acid phenyl ester was obtained as a colorless solid with an m.p. of 44-46° C. in a yield of 5.58 g (100%).

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-cfe9fbec2eba452cb75703f4c5d2d1a3
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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