Potassium Carbonate → HCID 11178774, compound

HRID 1830606Notes

Reaction equation

HRID 1830606 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]([NH:24][CH3:25])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].[CH3:32][C:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>ClCCl.O>[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]([N:24]([CH3:25])[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:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:11][CH2:10]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 41892451-Methylcyclohexanecarbonyl chlorideHCID 58651185HCID 58651185, compound

Product 1

HCID 11178774HCID 11178774, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

To a solution of (2R)-1-[4-(2-methoxyphenyl)piperazin-1-yl]-N-methyl-3-pyridin-2-ylpropan-2-amine (90 mg.; 0.26 mmol, from Example 17) in dichloromethane (3 mL) at 0° C. was added a solution of potassium carbonate (180 mg.; 1.3 mmol) in water (0.5 mL), followed by a solution of 1-methyl-1-cyclohexanecarbonyl chloride (41 mg.; 0.26 mmol) in dichloromethane (0.5 mL). The reaction mixture was stirred while allowing to warm to ambient temperature over 1 hour, diluted with dichloromethane (5 mL), and the layers allowed to separate. The organic layer was dried over MgSO4, filtered, and the solvent removed in vacuo. The crude residue was purified by flash chromatography on silica gel (10% methanol/ethyl acetate) to yield the free base of the title compound as a clear oil (68 mg.; 56%). Treatment with an equimolar amount of fumaric acid in acetonitrile afforded the fumarate salt as a white crystalline solid, m.p. 145–146° C.; MS (+) ESI [M+H]+ @ m/z 465; 1H NMR, 400 MHz, DMSO-d6. Analysis for C28H40N4O2.C4H4O4 Calculated: C, 66.18; H, 7.64; N, 9.65 Found: C, 65.95; H, 7.41; N, 9.54

Workup

  1. customto separate
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed in vacuo
  5. customThe crude residue was purified by flash chromatography on silica gel (10% methanol/ethyl acetate)

Sources & evidence

ORD record
ord-a64a457f23fc4a749b8baf96ac732585
Source dataset
uspto-grants-2006_06
Patent number
US07067518B2

Reaction notes

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