Potassium Iodide → HCID 85873146, compound

HRID 748510Notes

Reaction equation

HRID 748510 reaction equation
C(N(C(C)C)CC)(C)C.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17]Cl)=[CH:13][N+:12]=1[O-:19].[C:20]1([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[I-].[K+].[N-]=C=O.C1(S)C=CC=CC=1.C(=O)([O-])[O-]>O1CCCC1.C(O)C>[Cl:10][C:11]1[N+:12]([O-:19])=[CH:13][C:14]([CH2:17][N:29]2[CH2:30][CH2:31][N:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:27][CH2:28]2)=[CH:15][CH:16]=1

Participants

10

Reactant 7

HCID 4875Potassium IodideHCID 70961-PhenylpiperazineHCID 7969ThiophenolHCID 19660Carbonate IonHCID 81531Diisopropylethylamine2×HCID 105034IsocyanateHCID 124874662-Chloro-5-chloromethylpyridine 1-oxide

Product 1

HCID 85873146HCID 85873146, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent7×

Procedure

PS-Diisopropylethylamine (3.54 mmol/g, 0.4 g, 1.40 mmol) was washed with tetrahydrofuran and 2-chloro-5-(chloromethyl)pyridine 1-oxide (100 mg, 0.56 mmol; described in: Tilley, J. W. et al, J. Heterocyclic Chem. 1979, 16, 333) was added followed by tetrahydrofuran (1 mL). A solution of 1-phenylpiperazine (182 mg, 1.12 mmol) in tetrahydrofuran (1 mL) and a catalytic amount of potassium iodide were added, and the mixture was gently stirred (100 r/min) at room temperature for one week. PS-Isocyanate (1.76 mmol/g, 0.80 g, 1.40 mmol) was washed with tetrahydrofuran and added to the mixture followed by additional tetrahydrofuran (1 mL). The suspension was gently stirred (100 r/min) at room temperature for 19 h. The suspension was filtered (20 μm polyethylene filter), and the resins were washed with methylene chloride, tetrahydrofuran, and ethanol. Volatiles were removed in vacuo, and the residue was suspended in a 1:1-mixture of tetrahydrofuran and ethanol (8 mL) followed by the addition of N-ethyl-N,N-diisopropylamine (50 μL, 0.28 mmol). The mixture was added to PS-Thiophenol (1.35 mmol/g, 0.21 g, 0.28 mmol), and MP-Carbonate (3.20 mmol/g, 90 mg, 0.28 mmol), both pre-swelled in tetrahydrofuran. The mixture was stirred (100 r/min) at room temperature overnight followed by filtration. The resins were washed with methylene chloride, tetrahydrofuran, and ethanol, and the filtrate was concentrated in vacuo to give 141 mg (83% yield) of the title compound: 1H NMR (CDCl3, 400 MHz) δ 8.42 (s, 1 H), 7.45 (d, J=8 Hz, 1 H), 7.30-7.26 (m, 2 H), 7.25-7.21 (m, 1 H), 6.95-6.90 (m, 2 H), 6.89-6.85 (m, 1 H), 3.51 (s, 2 H), 3.22-3.18 (m, 4 H), 2.65-2.60 (m, 4 H); MS (ES) m/z 304 (M++1).

Workup

  1. additionwas added
  2. additionadded to the mixture
  3. stirringThe suspension was gently stirred (100 r/min) at room temperature for 19 h
  4. filtrationThe suspension was filtered
  5. filtration(20 μm polyethylene filter)
  6. washthe resins were washed with methylene chloride, tetrahydrofuran, and ethanol
  7. customVolatiles were removed in vacuo
  8. stirringThe mixture was stirred (100 r/min) at room temperature overnight
  9. filtrationfollowed by filtration
  10. washThe resins were washed with methylene chloride, tetrahydrofuran, and ethanol
  11. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bb87f755b9194debb5abfabbbda1beb4
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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