Pyridine → HCID 60628064, compound

HRID 346811Notes

Reaction equation

HRID 346811 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 mmol.) and pyridine (1.74 g, 22.0 mmol.) were added to a solution of tryptamine (2-(1H-indol-3-yl)ethylamine, 3.2 g, 20.0 mmol.) in abs. DCM (50 ml), and stirring was carried out for 24 h at RT. For working up, the mixture was washed with water (2×20 ml), 1M HCl (2×20 ml) and 1M NaOH (2×20 ml), and the organic phase was dried, filtered and concentrated. [2-(1H-Indol-3-yl)ethyl]carbamic acid phenyl ester was obtained in a yield of 5.58 g (white solid, m.p. 44–46° C.).

Workup

  1. washthe mixture was washed with water (2×20 ml), 1M HCl (2×20 ml) and 1M NaOH (2×20 ml)
  2. customthe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fe4c5e9f38b64370a8411ae92d7dc40e
Source dataset
uspto-grants-2007_02
Patent number
US07173045B2

Reaction notes

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