Potassium Carbonate → HCID 15484897, compound

HRID 367041Notes

Reaction equation

HRID 367041 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2([N:15]3[CH2:20][CH2:19][N:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH2:17][CH2:16]3)[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.Br[CH2:28][CH2:29][O:30][CH2:31][CH2:32]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[O:30]1[CH2:31][CH2:32][N:1]([C:2]2[CH:3]=[C:4]([C:8]3([N:15]4[CH2:16][CH2:17][N:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH2:19][CH2:20]4)[CH2:13][CH2:12][CH:11]([CH3:14])[CH2:10][CH2:9]3)[CH:5]=[CH:6][CH:7]=2)[CH2:28][CH2:29]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 15434718HCID 15434718, compound

Product 1

HCID 15484897HCID 15484897, compoundYield 37.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

1-(3-Aminophenyl)-1-(4-phenylpiperazin-1-yl)-4-methyl cyclohexane (cis isomer) (150 mg) was dissolved in 1 mL dry DMF under a nitrogen atmosphere. 2-Bromoethyl ether (150 mg) and potassium carbonate (150 mg) were added and the mixture was heated to 90° C. for 6 hours. The mixture was cooled to room temperature, diluted with 20 mL ethyl acetate, and transferred to a separatory funnel. The mixture was washed 5×10 mL water and 1×10 mL brine. The organic phase was dried over sodium sulfate, filtered, and concentrated. The residue was purified by flash chromatography, eluting with 9/1 hexanes/ethyl acetate to give 68 mg 1-(3-morpholinophenyl)-1-(4-phenylpiperazin-1-yl)-4-methyl cyclohexane (cis isomer) as a clear oil. m.p. (HCl salt)=178-180° C.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customtransferred to a separatory funnel
  3. washThe mixture was washed 5×10 mL water and 1×10 mL brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 9/1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-f1beda02e5284e06ba681427288ecf78
Source dataset
uspto-grants-2000_10
Patent number
US06133265

Reaction notes

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