Hydrochloric Acid → HCID 68773988, compound

HRID 1969319Notes

Reaction equation

HRID 1969319 reaction equation
[F:1]/[C:2](/[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:3]/[CH2:4][NH:5]C(=O)OC(C)(C)C.[ClH:21]>C(OCC)C>[ClH:21].[F:1]/[C:2](/[CH2:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:3]/[CH2:4][NH2:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59588981HCID 59588981, compound

Product 1

HCID 68773988HCID 68773988, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of (E)-tert-butyl 3-fluoro-4-phenoxybut-2-enylcarbamate (0.026 g, 0.09 mmol) in diethyl ether (3 mL) was added HCl (2 M solution in diethyl ether; 0.23 mL) dropwise. The reaction mixture was then sealed and allowed to stand for 68 hours. The solvent was removed under reduced pressure, dissolved in methanol (2 mL), filtered, and the methanol removed. The resultant gum was dried at 60° C. to afford (E)-3-fluoro-4-phenoxybut-2-en-1-amine hydrochloride (0.009 g, 46%) as an off-white solid; m.p.=113-116° C.; 1H-NMR (200 MHz, CD3OD): δppm: 3.69 (2H, d, J 8.2 Hz), 4.75 (2H, d, J 17.8 Hz), 5.51 (1H, dt, J 18.2, 8.6 Hz), 6.91-7.03 (3H, m), 7.22-7.35 (2H, m).

Workup

  1. customThe reaction mixture was then sealed
  2. customThe solvent was removed under reduced pressure
  3. dissolutiondissolved in methanol (2 mL)
  4. filtrationfiltered
  5. customthe methanol removed
  6. customThe resultant gum was dried at 60° C.

Sources & evidence

ORD record
ord-b49824548f7b4ed99452f3e330569555
Source dataset
uspto-grants-2013_04
Patent number
US08426587B2

Reaction notes

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