Hydrochloric Acid → 2-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethanamine

HRID 1019507Notes

Reaction equation

HRID 1019507 reaction equation
[C:1]([CH2:3][CH:4]1[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][CH2:5]1)#[N:2].Cl>C1COCC1>[O:9]1[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][CH2:5][CH:4]1[CH2:3][CH2:1][NH2:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 2675312-(2,3-Dihydro-1,4-benzodioxin-2-yl)acetonitrile

Product 1

HCID 556482-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The 2-cyanomethyl-(2,3 dihydrobenzo[1,4]dioxine) was dissolved in THF (50 mL) and 1M BH3 in THF (80 mL, 80 mmol) was added and the reaction mixture refluxed for 5 h, then stirred at ambient temperature for 16 h. With ice bath cooling, 2N HCl was added until pH=1.0 was achieved. The reaction mixture was then stirred for 1 h at room temperature and evaporated in vacuo to yield an oil. The oil was partitioned between 3N NaOH and diethyl ether, and the diethyl ether solution was washed with brine, dried (Na2SO4) and evaporated in vacuo to yield crude 2-(2,3 dihydrobenzo[1,4]dioxin-2-yl)ethylamine.

Workup

  1. temperaturethe reaction mixture refluxed for 5 h
  2. temperatureWith ice bath cooling
  3. stirringThe reaction mixture was then stirred for 1 h at room temperature
  4. customevaporated in vacuo
  5. customto yield an oil
  6. customThe oil was partitioned between 3N NaOH and diethyl ether
  7. washthe diethyl ether solution was washed with brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-5b8d750885d34074a538aaedf75a9411
Source dataset
uspto-grants-2014_05
Patent number
US08716231B2

Reaction notes

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