Sodium Iodide → HCID 70873537, compound

HRID 2172224Notes

Reaction equation

HRID 2172224 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH2:14][CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN1C(=O)CCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][C:31]([F:32])([F:33])[F:34])=[CH:26][CH:25]=1)[CH2:14][CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2233929075893-80-0HCID 86709383HCID 86709383, compound

Product 1

HCID 70873537HCID 70873537, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6-Benzyloxy-1,2,3,4-tetrahydro-quinoline (1.20 g, 5 mmol), 1-(3-chloropropoxy)-4-trifluoromethoxybenzene (1.42 g, 5.58 mmol), potassium carbonate (1.04 g, 7.5 mmol) and sodium iodide (0.90 g, 6 mmol) were heated and stirred at 90° C. in NMP (10 ml) overnight. Water was added thereto, followed by extraction with ethyl acetate. The organic layer was washed with water and dried over sodium sulfate. The result was concentrated and purified by silica gel column chromatography (hexane:ethyl acetate=75:25) to afford the title compound as a yellow oil (2.13 g, 93%).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulfate
  4. concentrationThe result was concentrated
  5. custompurified by silica gel column chromatography (hexane:ethyl acetate=75:25)

Sources & evidence

ORD record
ord-bbaa5ceeebbb4b8b8e5055725557e5b8
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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