Hydrochloric Acid → HCID 22176549, compound

HRID 1797217Notes

Reaction equation

HRID 1797217 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([O:14][Si](C)(C)C)([CH3:13])[C:11]#[N:12].[ClH:19]>C1COCC1.C(OCC)C>[ClH:19].[F:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([OH:14])([CH3:13])[CH2:11][NH2:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 221765932-(2-Fluoro-4-methoxy-phenyl)-2-trimethylsilanyloxy-propionitrile

Product 1

HCID 22176549HCID 22176549, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-(2-Fluoro-4-methoxy-phenyl)-2-trimethylsilanyloxy-propionitrile (2.8 g, 10.47 mmol) was dissolved in dry THF (30 mL) and stirred at room temperature under nitrogen. A 2.0 M solution of borane-dimethylsulfide complex (15.7 mL, 31.41 mmol) was added dropwise and the reaction was heated at reflux for 3 hours then cooled to room temperature. Concentrated HCl was carefully added dropwise until the evolution of gas ceased. The reaction mixture was diluted with diethyl ether and a white precipitate formed. The solids were collected and washed with additional ether to give 2.5 g (100%) of 2-(2-fluoro-4-methoxy-phenyl)-2-hydroxy-propylamine hydrochloride. Electrospray mass spectrum (M−1)=199.99 (free amine)

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 3 hours
  3. temperaturethen cooled to room temperature
  4. customa white precipitate formed
  5. customThe solids were collected
  6. washwashed with additional ether

Sources & evidence

ORD record
ord-77a90747ba6f4c008f3d6264e62c7b4b
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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