Hydrochloric Acid → HCID 58651186, compound

HRID 1830599Notes

Reaction equation

HRID 1830599 reaction equation
[NH2:1][C@H:2]([CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[C:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[O:17][CH3:18])[CH2:7][CH2:6]1)=O.B.C1COCC1.Cl>C1COCC1.O>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:8]1[CH2:9][CH2:10][N:5]([CH2:3][C@H:2]([NH2:1])[CH2:19][C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 58651193HCID 58651193, compound

Product 1

HCID 58651186HCID 58651186, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R)-2-Amino-1-[4-(2-methoxy-phenyl)-piperazin-1-yl]-3-pyridin-4-yl-propan-1-one (6.18 g; 18 mmol, from Example 7) in THF (60 mL) was added, dropwise, BH3.THF (1.0M/THF) (73 mL; 73 mmol). The mixture was stirred at reflux for 2 hours, cooled to ambient temperature, cautiously treated with 6N HCl (45 mL), stirred at ambient temperature for 1 hours. The mixture was then diluted with water (100 mL), concentrated on a rotary evaporator to remove THF, and the aqueous residue washed with ether (30 mL). The aqueous layer was rendered basic (pH 9–10) with concentrated NH4OH, and the product extracted into dichloromethane (3×75 mL). The combined dichloromethane layers were washed with brine, dried over MgSO4, filtered, and the solvent removed in vacuo to yield the title compound as a free base (4.85 g.; 82%). The analytical sample was converted to the hydrochloride salt with ethereal HCl to yield an off-white crystalline solid, m.p. 177–178° C.; MS (+) ESI, [M+H]+ @ m/z 327; 1H NMR, 400 MHz, DMSO-d6. Analysis for C19H26N4O.HCl.0.3H2O.0.3 C2H6O Calculated: C, 61.61; H, 7.75; N, 14.66 Found: C, 61.45; H, 7.80; N, 14.49.

Workup

  1. temperatureat reflux for 2 hours
  2. stirringstirred at ambient temperature for 1 hours
  3. concentrationconcentrated on a rotary evaporator
  4. customto remove THF
  5. washthe aqueous residue washed with ether (30 mL)
  6. extractionthe product extracted into dichloromethane (3×75 mL)
  7. washThe combined dichloromethane layers were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2820937dbf344fc384c58b111ad012b4
Source dataset
uspto-grants-2006_06
Patent number
US07067518B2

Reaction notes

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