Triethylamine → HCID 11293507, compound

HRID 1830600Notes

Reaction equation

HRID 1830600 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C@H:16]([NH2:24])[CH2:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH2:11][CH2:10]1.C(N(CC)CC)C.[CH:32]1([C:38](Cl)=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][C@H:16]([NH:24][C:38]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[O:39])[CH2:17][C:18]2[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 58651186HCID 58651186, compound

Product 1

HCID 11293507HCID 11293507, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R)-2-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-1-pyridin-4-ylmethyl-ethylamine (800 mg.; 2.45 mmol, from Example 8) in dichloromethane (30 mL) at 0° C. was added triethylamine (0.68 mL; 4.9 mmol) and cyclohexanecarbonyl chloride (0.33 mL; 2.45 mmol). The reaction mixture was stirred while allowing to warm to ambient temperature over 1 hour. The mixture was washed with saturated NaHCO3 (5 mL), dried over MgSO4, filtered, and the solvent removed in vacuo. The crude residue was purified by flash chromatography on silica gel (2% methanol/chloroform) to afford the free base of the title compound as a white gummy foam (610 mg; 57%). Treatment with an equimolar amount of maleic acid in ethanol yielded the maleate salt as an off-white amorphous solid, m.p. 145–147° C.; MS (+) FAB [M+H]+ @ m/z 437, [M+Na]+ @ m/z 459; 1H NMR, 400 MHz, DMSO-d6. Analysis for C26H36N4O2.C4H4O4.0.5H2O Calculated: C, 64.15; H, 7.36; N, 9.97 Found: C, 64.23; H, 7.37; N, 9.88

Workup

  1. washThe mixture was washed with saturated NaHCO3 (5 mL)
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe crude residue was purified by flash chromatography on silica gel (2% methanol/chloroform)

Sources & evidence

ORD record
ord-da5a8ef044cc4ebfbeb2b0224549fee0
Source dataset
uspto-grants-2006_06
Patent number
US07067518B2

Reaction notes

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