Hydrochloric Acid → HCID 58651193, compound

HRID 1830598Notes

Reaction equation

HRID 1830598 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=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:31]=[CH:30][N:29]=[CH:28][CH:27]=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 58651184HCID 58651184, compound

Product 1

HCID 58651193HCID 58651193, 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-4-ylmethyl-ethyl}-carbamic acid tert-butyl ester (7.96 g.; 18 mmol) from Example 6 in THF (60 mL) at 0° C. was added HCl (4M/Dioxane) (74 mL; 0.3 mol). The mixture was stirred at ambient temperature for 3 hours, and the solvent removed in vacuo. The residue was dissolved in water (70 mL), washed with ether (40 mL). 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 (6.12 g., 100%). An analytical sample was prepared by treatment with ethereal HCl to yield the hydrochloride salt as an off-white crystalline solid, m.p. >175–177° C.; MS (+) ESI, [M+H]+ @ m/z 341; 1H NMR, 400 MHz, DMSO-d6. Analysis for C19H24N4O2.1.1HCl.0.5H2O Calculated: C, 58.58; H, 6.75; N, 14.38 Found: C, 58.64; H, 6.46; N, 14.25.

Workup

  1. customthe solvent removed in vacuo
  2. dissolutionThe 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-394bed6c7a724966b7e354c15e80ab46
Source dataset
uspto-grants-2006_06
Patent number
US07067518B2

Reaction notes

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