Hydrochloric Acid → 4-Fluoro-2-[(methylamino)carbonyl]benzylamine hydrochloride

HRID 2252802Notes

Reaction equation

HRID 2252802 reaction equation
[ClH:1].[F:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH:8]C(=O)OC(C)(C)C)=[C:5]([C:18]([NH:20][CH3:21])=[O:19])[CH:4]=1>C(OCC)(=O)C>[Cl-:1].[F:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][NH3+:8])=[C:5]([C:18]([NH:20][CH3:21])=[O:19])[CH:4]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11984298Tert-butyl 4-fluoro-2-[(methylamino)carbonyl]benzylcarbamate

Product 1

HCID 866001764-Fluoro-2-[(methylamino)carbonyl]benzylamine hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydrogen chloride gas was bubbled through a −78° C. solution of tert-butyl 4-fluoro-2-[(methylamino)carbonyl]benzylcarbamate (615 mg, 2.18 mmol) in ethyl acetate (20 mL) until the solution was saturated. The flask was then allowed to warm to room temperature. The reaction was concentrated in vacud to a volume of about 5 mL and the flask was capped and placed in the freezer overnight. In the morning, the solids that had precipitated were collected by vacuum filtration and washed with cold ethyl acetate to give the desired product as an off-white solid.

Workup

  1. concentrationThe reaction was concentrated in vacud to a volume of about 5 mL
  2. customthe flask was capped
  3. customplaced in the freezer overnight
  4. customIn the morning, the solids that had precipitated
  5. filtrationwere collected by vacuum filtration
  6. washwashed with cold ethyl acetate

Sources & evidence

ORD record
ord-354251217b304402ba879c1a01c4710c
Source dataset
uspto-grants-2008_01
Patent number
US07323460B2

Reaction notes

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