Hydrochloric Acid → (S)-1-[3-(4-Pyridin-2-ylpiperazin-1-yl)phenyl]ethylamine

HRID 7592Notes

Reaction equation

HRID 7592 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=3)[CH2:18][CH2:17]2)[CH:11]=1)[CH3:9])(C)(C)C.Cl>O1CCOCC1>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[N:19]1[CH2:20][CH2:21][N:16]([C:12]2[CH:11]=[C:10]([C@@H:8]([NH2:7])[CH3:9])[CH:15]=[CH:14][CH:13]=2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58680161(S)-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}carbamic acid tert-butyl ester

Product 1

HCID 58680156(S)-1-[3-(4-Pyridin-2-ylpiperazin-1-yl)phenyl]ethylamineYield 89.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of (S)-{1-[3-(4-pyridin-2-ylpiperazin-1-yl)phenyl]ethyl}carbamic acid tert-butyl ester (4.1 g, 10.7 mmol) and hydrochloric acid (4N, 11 mL) in dioxane (40 mL) was stirred at 40° C. for 5 h. The reaction mixture was concentrated under vacuum, dissolved into water (50 mL), and washed with dichloromethane (2×50 mL). The aqueous layer was based with 5N NaOH and extracted with dichloromethane (3×100 mL). The combined organic layers were washed with brine (2×100 ml), dried over sodium sulfate and concentrated under vacuum to afford the title compound as an oil (2.70 g, 89% yield).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. dissolutiondissolved into water (50 mL)
  3. washwashed with dichloromethane (2×50 mL)
  4. extractionextracted with dichloromethane (3×100 mL)
  5. washThe combined organic layers were washed with brine (2×100 ml)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-96a4cec411f14a0684b762b320f4b158
Source dataset
uspto-grants-2006_08
Patent number
US07087609B2

Reaction notes

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