Pyridine → HCID 60628064, compound

HRID 1394236Notes

Reaction equation

HRID 1394236 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 CH2Cl2 and stirred for 24 h at room temperature. Working up was performed by extracting the batch successively with water, with 1M HCl and with 1M NaOH. The organic phase was dried with Na2SO4 and evaporated. The product was obtained as a colorless solid (m.p. 44-46° C.) in a yield of 5.58 g (100%).

Workup

  1. extractionby extracting the batch successively with water
  2. dry with materialThe organic phase was dried with Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-57d010efb638482492c4d8e89cf21259
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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