Monobasic potassium phosphate → HCID 21187594, compound

HRID 1383332Notes

Reaction equation

HRID 1383332 reaction equation
ClC(Cl)(Cl)COC([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:21]=[CH:20][CH:19]=[C:18]3[C:14]=2[CH:15]=[C:16]([CH3:22])[NH:17]3)[CH2:9][CH2:8]1)=O.OP([O-])(O)=O.[K+]>[Zn].O1CCCC1>[CH3:22][C:16]1[NH:17][C:18]2[C:14]([CH:15]=1)=[C:13]([N:10]1[CH2:11][CH2:12][NH:7][CH2:8][CH2:9]1)[CH:21]=[CH:20][CH:19]=2

Participants

5

Reactant 2

HCID 516951Monobasic potassium phosphateHCID 21187589HCID 21187589, compound

Product 1

HCID 21187594HCID 21187594, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(2,2,2-trichloroethoxycarbonyl)-1-(2-methyl-1H-indol-4-yl)piperazine (0.70 g, 1.79 mmol, used directly from above), zinc dust (2.0 g), tetrahydrofuran (15 mL), and a solution of KH2PO4 (1.0 M, 3 mL) was vigorously stirred at room temperature under nitrogen for 6 hours. The resulting reaction mixture was filtered, and the filtrate was evaporated under reduced pressure. The residue was chromatographed using silica gel (approximately 75 g) and elution with methylene chloride/methanol/ammonium hydroxide [6:1:0.1] to afford the title compound (0.170 g, 0.79 mmol, 44%) as an off-white amorphous solid: Rf=0.2 in methylene chloride/methanol/ammonium hydroxide [6:1:0.1]; 1H NMR (CD3OD) δ7.02 (d, J=8.0 Hz, 1H), 6.94 (t, J=7.7 Hz, 1H), 6.54 (dd, J=1.0 and 7.3 Hz, 1H), 6.15 (s, 1H), 4.89 (s, exchangeable protons), 3.43 (br t, 4H), 3.40 (br t, 4H), 2.41 (s, 3H).

Workup

  1. customThe resulting reaction mixture
  2. filtrationwas filtered
  3. customthe filtrate was evaporated under reduced pressure
  4. customThe residue was chromatographed
  5. washsilica gel (approximately 75 g) and elution with methylene chloride/methanol/ammonium hydroxide [6:1:0.1]

Sources & evidence

ORD record
ord-0563ef8daa18427ba0ae799424bccfe7
Source dataset
uspto-grants-2001_07
Patent number
US06255306B1

Reaction notes

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