Triethylamine → HCID 11339906, compound

HRID 1830597Notes

Reaction equation

HRID 1830597 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:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:11][CH2:10]1.C(N(CC)CC)C.[CH3:32][C:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]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:39]([C:33]2([CH3:32])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]2)=[O:40])[CH2:17][C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 41892451-Methylcyclohexanecarbonyl chlorideHCID 58651188HCID 58651188, compound

Product 1

HCID 11339906HCID 11339906, compoundYield 29.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R)-2-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-1-pyridin-3-ylmethyl-ethylamine (326 mg.; 1 mmol, from Example 3) in dichloromethane (15 mL) at 0° C. was added triethylamine (0.28 mL; 2 mmol) and 1-methyl-1-cyclohexanecarbonyl chloride (160 mg.; 1 mmol). The reaction mixture was stirred while allowing to warm to ambient temperature over 1 hour, washed sequentially with saturated aqueous NaHCO3 and brine, dried over MgSO4, filtered, and the solvent removed in vacuo. The crude residue was purified by flash chromatography on silica gel (5% methanol/chloroform) to yield the free base of the title compound as a clear oil (132 mg.; 29%). Treatment with an equimolar amount of fumaric acid in ethanol afforded the fumarate salt as an off-white amorphous solid, m.p. 150–152° C.; MS (+) FAB, [M+H]+ @ m/z 451, [M+Na]+ @ m/z 473; 1H NMR, 400 MHz, DMSO-d6. Analysis for C27H38N4O2.C4H4O4.0.5H2O Calculated: C, 64.68; H, 7.53; N, 9.73 Found: C, 64.89; H, 7.18; N, 9.64.

Workup

  1. washwashed sequentially with saturated aqueous NaHCO3 and brine
  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 (5% methanol/chloroform)

Sources & evidence

ORD record
ord-9d4baf9b3b634fbb80e93344059e4a88
Source dataset
uspto-grants-2006_06
Patent number
US07067518B2

Reaction notes

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