Hydrochloric Acid → HCID 21073537, compound

HRID 1373617Notes

Reaction equation

HRID 1373617 reaction equation
C(O[C:6](=[O:35])[NH:7][CH2:8][C:9]1[C:10]([NH2:34])=[N:11][C:12]([O:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]2[CH2:25][CH2:24][N:23]([C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=3[Cl:33])[CH2:22][CH2:21]2)=[CH:13][CH:14]=1)(C)(C)C.Cl.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1>[Cl:33][C:27]1[C:28]([Cl:32])=[CH:29][CH:30]=[CH:31][C:26]=1[N:23]1[CH2:22][CH2:21][N:20]([CH2:19][CH2:18][CH2:17][CH2:16][O:15][C:12]2[CH:13]=[CH:14][C:9]3[CH2:8][NH:7][C:6](=[O:35])[NH:34][C:10]=3[N:11]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 69417410HCID 69417410, compound

Product 1

HCID 21073537HCID 21073537, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of crude (2-amino-6-{4-[4-(2,3-dichloro-phenyl)-piperazin-1-yl]-butoxy}-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester in dioxane (15 mL) was added 3 N HCl (15 mL). The resulting mixture was refluxed for 2 hours, cooled to RT, then neutralized with saturated Na2CO3. The neutralized solution was extracted with EtOAc and the organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to afford the title compound as a brown oil (0.367 g, 94% over two steps). 1H NMR (400 MHz, CDCl3): δ 7.21–7.10 (m, 3H), 7.00–6.91 (m, 1H), 6.00 (d, 1H), 5.40–5.21 (br s, 2H), 4.12 (t, 2H), 3.82 (s, 2H), 3.71 (s, 2H), 3.19–2.98 (m, 4H), 2.81–2.55 (m, 4H), 2.50 (t, 2H), 1.91–1.43 (m, 4H). MS ES: m/z=424.00, 425.99.

Workup

  1. temperatureThe resulting mixture was refluxed for 2 hours
  2. extractionThe neutralized solution was extracted with EtOAc
  3. washthe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdb72c74d9e94a28a69a276997e86816
Source dataset
uspto-grants-2007_01
Patent number
US07160888B2

Reaction notes

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