Hydrochloric Acid → (S)-1-[3-(Pyridin-2-yloxyl)-phenyl]-ethylamine

HRID 2183456Notes

Reaction equation

HRID 2183456 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]=[CH: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][CH: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 60004110HCID 60004110, compound

Product 1

HCID 20791741(S)-1-[3-(Pyridin-2-yloxyl)-phenyl]-ethylamineYield 99%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of (S)-{1-[3-(pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (5 g, 16 mmol), dioxane (80 mL) and HCl (64 mL, 4N) was stirred at 50° C. for 4 h and concentrated in vacuo then CH2Cl2 (100 mL) was added and the reaction mixture was basified with NaOH (5N) followed by extraction with CH2Cl2 (2×100 mL). The organic layer was washed with brine (100 mL), dried over anhydrous magnesium sulfate and filtered, and the filtrate was concentrated to give the title compound (3.39 g, 99% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. additionCH2Cl2 (100 mL) was added
  3. extractionfollowed by extraction with CH2Cl2 (2×100 mL)
  4. washThe organic layer was washed with brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-0d0e4e549eb94019b94274ce395599b1
Source dataset
uspto-grants-2005_05
Patent number
US06900210B2

Reaction notes

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