Pyridine → HCID 12986252, compound

HRID 1394234Notes

Reaction equation

HRID 1394234 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.[C:17]1([CH2:23][CH2:24][CH2:25][NH2:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(Cl)Cl>[C:1]1([O:7][C:8](=[O:9])[NH:26][CH2:25][CH2:24][CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 162593-Phenylpropylamine

Product 1

HCID 12986252HCID 12986252, 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 3-phenylpropylamine (2.7 g, 20.0 mmole) in CH2Cl2 and stirred for 24 h at room temperature. Working up was performed by extracting the batch successively with H2O, 1M HCl and 1M NaOH. The organic phase was dried with Na2SO4 and evaporated. The product was obtained as a colorless solid (m.p. 55-56° C.) in a yield of 4.11 g (81%) by recrystallisation from ethyl acetate/hexane (1:1).

Workup

  1. extractionby extracting the batch successively with H2O, 1M HCl and 1M NaOH
  2. dry with materialThe organic phase was dried with Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-96edc421ab8740dd9f68e62ddf352ccc
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

Loading…