Triethylamine → HCID 11407942, compound

HRID 1830604Notes

Reaction equation

HRID 1830604 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][CH:21]=[CH:20][N: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:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 58651192HCID 58651192, compound

Product 1

HCID 11407942HCID 11407942, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (1R)-2-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-1-pyridin-2-ylmethyl-ethylamine (780 mg.; 2.4 mmol, from Example 13) in dichloromethane (30 mL) at 0° C. was added triethylamine (0.67 mL; 4.8 mmol) and a solution of cyclohexanecarbonyl chloride (0.33 mL; 2.45 mmol) in dichloromethane (5 mL). The reaction mixture was stirred while allowing to warm to ambient temperature over 1 hour. The mixture was washed with saturated NaHCO3 (15 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 (750 mg; 72%). Treatment with an equimolar amount of fumaric acid in ethanol yielded the fumarate salt as a white amorphous solid, m.p. 136–141° C.; MS (+) FAB [M+H]+ @ m/z 437, [M+Na]+ @ m/z 459; 1H NMR, 400 MHz, DMSO-d6. Analysis for C26H36N4O2. C4H4O4.2H2O Calculated: C, 61.21; H, 7.53; N, 9.52 Found: C, 61.79; H, 7.27; N, 9.31

Workup

  1. washThe mixture was washed with saturated NaHCO3 (15 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-8b4c91490baf4d2f9628f2d856246150
Source dataset
uspto-grants-2006_06
Patent number
US07067518B2

Reaction notes

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