Hydrochloric Acid → (S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethanamine

HRID 57433Notes

Reaction equation

HRID 57433 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:5]=[CH:4][C:3]=1[C@@H:11]([NH:13][S@@](C(C)(C)C)=O)[CH3:12].[ClH:20]>O1CCOCC1>[ClH:20].[F:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:10])=[CH2:9])[CH:5]=[CH:4][C:3]=1[C@@H:11]([NH2:13])[CH3:12]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86730187(R)-N-((S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethyl)-2-methylpropane-2-sulfinamide

Product 2

HCID 313Hydrochloric AcidHCID 90415150(S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethanamineYield 96%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a round bottom flask containing (R)—N—((S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethyl)-2-methylpropane-2-sulfinamide (1.02 g, 3.60 mmol) was added dioxane (7 mL). To this homogenous solution was then added HCl in Dioxane (1.80 mL, 7.20 mmol, 4 M). Resulting reaction mixture allowed to stir 10 min at room temperature. Volatiles removed. Et2O was added and mixture sonnicated briefly. Volatiles removed again. Et2O was added and the solid collected and washed with Et2O to afford a white HCl salt of (S)-1-(2-fluoro-4-(prop-1-en-2-yl)phenyl)ethanamine (742 mg, 3.44 mmol, 96% yield). 1H NMR (400 MHz, D2O) δ 1.65 (d, J=6.94 Hz, 3H) 2.12 (s, 3H) 5.23 (s, 1H) 5.50 (s, 1H) 7.37 (d, J=13.06 Hz, 1H) 7.43 (m, 2H). LCMS m/z 163.2 (deamino fragment) (M+H)+, Rt 0.56 min.

Workup

  1. customResulting
  2. customreaction mixture
  3. customVolatiles removed
  4. additionEt2O was added
  5. customVolatiles removed again
  6. additionEt2O was added
  7. customthe solid collected
  8. washwashed with Et2O

Sources & evidence

ORD record
ord-2e3de750ceaa468fa0382b6ea5d225be
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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