Hydrochloric Acid → 2-(1-Piperazinyl)-3-{2-[3-(4-morpholinylmethyl)phenoxy]ethoxy}pyrazine

HRID 353711Notes

Reaction equation

HRID 353711 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:34]=[CH:35][CH:36]=2)[O:11][CH2:12][CH2:13][O:14][C:15]2[C:16]([N:21]3[CH2:26][CH2:25][N:24](C(OC(C)(C)C)=O)[CH2:23][CH2:22]3)=[N:17][CH:18]=[CH:19][N:20]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Cl>CCOCC>[N:21]1([C:16]2[C:15]([O:14][CH2:13][CH2:12][O:11][C:10]3[CH:34]=[CH:35][CH:36]=[C:8]([CH2:7][N:1]4[CH2:6][CH2:5][O:4][CH2:3][CH2:2]4)[CH:9]=3)=[N:20][CH:19]=[CH:18][N:17]=2)[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11271979tert-Butyl4-(3-{2-[3-(4-morpholinylmethyl)phenoxy]ethoxy}-2-pyrazinyl)-1-piperazinecarboxylate

Product 1

HCID 101355682-(1-Piperazinyl)-3-{2-[3-(4-morpholinylmethyl)phenoxy]ethoxy}pyrazineYield 29%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

The product from step 4 above (54 mg, 0.1 1 mmol) was dissolved in dry ether (20 mL), stirred at room temperature and treated with hydrogen chloride in ether (˜6 M; 5 mL). The resulting white suspension was stirred for 2 h, then quickly filtered off. The hydrochloride salt (hygroscopic), was dissolved in water and neutralized with sodium carbonate. The free base was extracted into dichloromethane. The organic layers were dried magnesium sulfat, filtered, and concentrated in vacuo to furnish 13 mg (29%) of the title product as a pale yellow oil. LS/MS purity 100%. 1H NMR (CDCl3) δ 1.8 (b, 1H); 2.45 (m, 4H); 2.95 (m, 4H); 3.45 (s, 2H); 3.55 (m, 4H); 3.7 (m, 4H); 4.35 (t, 2H); 4.7 (t, 2H); 6.85 (d, 1H); 6.95 (m, 2H); 7.25 (t, 1H); 7.55 (s, 1H); 7.75 (s, 1H).

Workup

  1. stirringThe resulting white suspension was stirred for 2 h
  2. filtrationquickly filtered off
  3. dissolutionThe hydrochloride salt (hygroscopic), was dissolved in water and neutralized with sodium carbonate
  4. extractionThe free base was extracted into dichloromethane
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be8ba8015f6646d0b561789cc27c4b7c
Source dataset
uspto-grants-2004_06
Patent number
US06756377B2

Reaction notes

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