Sodium Bicarbonate → 2-Fluoro-6-cinnamylbenzylamine

HRID 2390045Notes

Reaction equation

HRID 2390045 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:3]=1[CH2:4][NH:5]C(=O)OC(C)(C)C.C(=O)(O)[O-].[Na+]>Cl.C(OCC)(=O)C>[F:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][CH:18]=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:3]=1[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68521872t-butyl N-(2-fluoro-6-cinnamylbenzyl)carbamate

Product 1

HCID 685218602-Fluoro-6-cinnamylbenzylamine

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

34 mg of t-butyl N-(2-fluoro-6-cinnamylbenzyl)carbamate was dissolved in a 4N hydrochloric acid/ethyl acetate solution, followed by stirring at room temperature for 1 hour. After completion of the reaction, to the reaction liquid was added an aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate, and the organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain 24 mg of a crude composition of 2-fluoro-6-cinnamylbenzylamine as a light yellow oily substance. The obtained crude composition, 19 mg of 2-methoxycarbonylethylsulfonylchloride, and 21 mg of sodium carbonate were dissolved in 1 mL of methylene chloride and 1 mL of water, followed by stirring under ice-cooling for 1 hour. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (n-hexane:ethyl acetate=2:1) to obtain 29 mg (yield 79%) of a title compound as a yellow solid.

Workup

  1. customAfter completion of the reaction
  2. customto the reaction liquid
  3. extractionfollowed by extraction with ethyl acetate
  4. washthe organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5792040eb650461292a0543b7808c9cb
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

Loading…