Potassium Iodide → HCID 18327332, compound

HRID 1250230Notes

Reaction equation

HRID 1250230 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[N:9]([CH2:14][CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)[C:8]2=[O:23].Cl.Cl[CH2:26][CH2:27][CH2:28][N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C1COCC1.O.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([CH3:13])[N:9]([CH2:14][CH2:15][CH2:16][CH:17]1[CH2:18][CH2:19][N:20]([CH2:26][CH2:27][CH2:28][N:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH2:21][CH2:22]1)[C:8]2=[O:23]

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 79624N-(3-chloropropyl)piperidine hydrochlorideHCID 18327317HCID 18327317, compound

Product 1

HCID 18327332HCID 18327332, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A mixture of the product from Step B (331 mg, 0.94 mmol), N-(3-chloropropyl)piperidine hydrochloride (666 mg, 1.88 mmol), potassium carbonate (260 mg, 1.88 mmol) and potassium iodide (312 mg, 1.88 mmol) in THF/H2O (3:1 mixture, 40 mL) was heated under reflux for 17 h. The reaction mixture was cooled to room temperature and diluted with EtOAc. The organic solution was washed with sat'd aq NaHCO3, sat'd aq brine, dried and concentrated. The crude residue was chromatographed on SiO2-gel using a solvent gradient of 100% EtOAc to EtOAc/NEt3 (10:1) to give the product as a yellow oil. API-MS: 441 (M+1). 1H NMR (300 MHz, CDCl3): d 7.8 (d, 1 H), 7.3 (t, 1 H), 7.1 (d, 1 H), 4.03 (t, 2 H), 4.9 (s, 3 H), 3.9 (m), 2.7 (s, 3 H), 2.3 (m), 1.8-1.2 (m).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 h
  3. washThe organic solution was washed with sat'd aq NaHCO3
  4. customdried
  5. concentrationconcentrated
  6. customThe crude residue was chromatographed on SiO2-gel

Sources & evidence

ORD record
ord-2bba0ef678aa4c41b713634d5c2d6166
Source dataset
uspto-grants-2002_01
Patent number
US06337332B1

Reaction notes

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