Hydrochloric Acid → (S)-1-[3-(pyrazin-2-yloxy)-phenyl]-ethylamine

HRID 2183461Notes

Reaction equation

HRID 2183461 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][C:17]2[CH:22]=[N:21][CH:20]=[CH:19][N:18]=2)[CH:11]=1)[CH3:9])(C)(C)C.Cl>O1CCOCC1>[N:18]1[CH:19]=[CH:20][N:21]=[CH:22][C:17]=1[O:16][C:12]1[CH:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 60004116HCID 60004116, compound

Product 1

HCID 60004137(S)-1-[3-(pyrazin-2-yloxy)-phenyl]-ethylamineYield 85.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (S)-{1-[3-(pyrazin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (1.33 g, 4.2 mmol), dioxane (20 mL) and HCl (4.2 mL, 4N) was stirred at 50° C. for 5 h and concentrated in vacuo. CH2Cl2 (50 mL) was added and the reaction mixture was basified with NaOH (5N) followed by extraction with CH2Cl2 (2×50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated to give the title compound (0.77 g, 85% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. additionCH2Cl2 (50 mL) was added
  3. extractionfollowed by extraction with CH2Cl2 (2×50 mL)
  4. washThe organic layer was washed with brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-372f248e6d3541dda5ff46ae3950e3c4
Source dataset
uspto-grants-2005_05
Patent number
US06900210B2

Reaction notes

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