Hydrochloric Acid → HCID 58651191, compound

HRID 1830595Notes

Reaction equation

HRID 1830595 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])(C)(C)C.Cl>C1COCC1>[NH2:7][C@H:8]([CH2:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)[C:9]([N:11]1[CH2:12][CH2:13][N:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[O:23][CH3:24])[CH2:15][CH2:16]1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58651189HCID 58651189, compound

Product 1

HCID 58651191HCID 58651191, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-{2-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-2-oxo-1-pyridin-3-ylmethyl-ethyl}-carbamic acid tert-butyl ester (7.54 g.; 17.1 mmol) from Example 1 in THF (60 mL) at 0° C. was added HCl (4M/Dioxane) (70 mL; 0.28 mol). The mixture was stirred at ambient temperature for 3 hours, and the solvent removed in vacuo. A small portion of the trihydrochloride residue was retained for analytical purposes. The remainder of the residue was dissolved in water (70 mL), washed with ether (40 mL), and the ether layer discarded. The aqueous layer was rendered basic (pH 9–10) with saturated aqueous Na2CO3, and the product extracted into dichloromethane (3×60 mL). The combined dichloromethane layers were washed with brine, dried over MgSO4, filtered, and the solvent removed in vacuo to afford the free base of the title compound as a clear oil (5.8 g., 100%). The analytical sample as the trihydrochloride salt was recrystallized from ethanol/ether to afford a white crystalline powder, m.p. >240° C.; MS (+) ESI, [M+H]+ @ m/z 341; 1H NMR, 400 MHz, DMSO-d6. Analysis for C19H24N4O2.3HCl Calculated: C, 50.73; H, 6.05; N, 12.46 Found: C, 50.89; H, 6.03; N, 12.41.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe remainder of the residue was dissolved in water (70 mL)
  3. washwashed with ether (40 mL)
  4. extractionthe product extracted into dichloromethane (3×60 mL)
  5. washThe combined dichloromethane layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-495323fdd3704771b3e60ba542529055
Source dataset
uspto-grants-2006_06
Patent number
US07067518B2

Reaction notes

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