Tetrahydrofuran → 2-(4-Chloro-2-methoxyphenyl)ethanamine

HRID 510585Notes

Reaction equation

HRID 510585 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][C:10]#[N:11].[O:12]1CCC[CH2:13]1>B>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][CH2:10][NH2:11])=[C:2]([O:12][CH3:13])[CH:7]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 218285012-(2-Bromo-4-chlorophenyl)acetonitrile

Product 1

HCID 582446162-(4-Chloro-2-methoxyphenyl)ethanamine

Reagents, catalysts & solvents 1

HCID 6331BoraneSolvent

Procedure

A portion of 2-(2-bromo-4-chlorophenyl)acetonitrile (7.1 g; 39.1 mmol) was directly dissolved in borane solution (78.2 mL of a 1.0 M solution in tetrahydrofuran; 78.2 mmol), and the resulting solution was stirred and heated to reflux. After refluxing for a total of 90 minutes, the heat was removed and the solution was allowed to cool for a few minutes, and then 16 mL of methanol was carefully added to quench the solution. The resulting solution was again heated to reflux for 30 minutes. The solvent was then evaporated, and the residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether. The aqueous layer was filtered to remove a small amount of suspended insoluble material, and the pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.). The filtrate was then extracted with 200 mL dichloromethane. The organic layer was dried over sodium sulfate and evaporated to give 3.89 g of 2-(4-chloro-2-methoxyphenyl)ethanamine as a colorless liquid. MS (apci, pos) m/z=186.

Workup

  1. temperatureheated to reflux
  2. temperatureAfter refluxing for a total of 90 minutes
  3. customthe heat was removed
  4. temperatureto cool for a few minutes
  5. addition16 mL of methanol was carefully added
  6. customto quench the solution
  7. temperatureThe resulting solution was again heated
  8. temperatureto reflux for 30 minutes
  9. customThe solvent was then evaporated
  10. customthe residue was partitioned between 200 mL of 1M HCl (aq.) and 200 mL ether
  11. filtrationThe aqueous layer was filtered
  12. customto remove a small amount of suspended insoluble material
  13. additionthe pH of the filtrate was adjusted to pH>12 by the addition of 42% NaOH (aq.)
  14. extractionThe filtrate was then extracted with 200 mL dichloromethane
  15. dry with materialThe organic layer was dried over sodium sulfate
  16. customevaporated

Sources & evidence

ORD record
ord-0a4d1aa8abba4f5d94a28877c7a20e73
Source dataset
uspto-grants-2015_08
Patent number
US09096567B2

Reaction notes

Loading…