Pyridinium chloride → HCID 22144882, compound

HRID 1824955Notes

Reaction equation

HRID 1824955 reaction equation
C(OC([NH:8][CH:9]([CH3:22])[CH2:10][C:11]1[C:19]2[O:18][CH:17]=[CH:16][C:15]=2[CH:14]=[C:13]([O:20]C)[CH:12]=1)=O)(C)(C)C.[ClH:23].N1C=CC=CC=1>ClCCl.[OH-].[NH4+]>[ClH:23].[OH:20][C:13]1[CH:12]=[C:11]([CH2:10][CH:9]([NH2:8])[CH3:22])[C:19]2[O:18][CH:17]=[CH:16][C:15]=2[CH:14]=1

Participants

5

Reactant 2

HCID 10176127Pyridinium chlorideHCID 22144812HCID 22144812, compound

Product 1

HCID 22144882HCID 22144882, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14923Ammonium HydroxideSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 0.73 gm (2.38 mMol) N-tert-butoxycarbonyl 1-(5-methoxybenzofur-7-yl)-2-aminopropane and 3.30 gm (28.52 mMol) pyridine hydrochloride were heated at 170° C. in a sealed tube for 15 hours. The mixture was cooled and the residue was dissolved in dichloromethane containing 10% methanol and 1% ammonium hydroxide. The solution was concentrated under reduced pressure and the pyridine remaining in the residue was removed azeotropically by diluting the residue with water and concentrating three times. The residue was crystallized from ethanol:diethyl ether. The 1-(5-hydroxybenzofur-7-yl)-2-aminopropane was recovered in the second crop and the filtrate. 0.045 gm (0.24 mMol) was treated with hydrochloric acid in diethyl ether to provide the title compound.

Workup

  1. temperatureThe mixture was cooled
  2. concentrationThe solution was concentrated under reduced pressure
  3. customthe pyridine remaining in the residue was removed azeotropically
  4. additionby diluting the residue with water
  5. concentrationconcentrating three times
  6. customThe residue was crystallized from ethanol
  7. customThe 1-(5-hydroxybenzofur-7-yl)-2-aminopropane was recovered in the second crop
  8. addition0.045 gm (0.24 mMol) was treated with hydrochloric acid in diethyl ether

Sources & evidence

ORD record
ord-2a037bc9ea6548599952c44c05742e6b
Source dataset
uspto-grants-2006_05
Patent number
US07045545B1

Reaction notes

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