Sodium Iodide → 1-[(3R)-3-(3,4-Dimethoxyphenoxy)-3-phenylpropyl]-4-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine

HRID 1832202Notes

Reaction equation

HRID 1832202 reaction equation
C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[N+:9]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH2:19][CH2:20][NH:21][CH2:22][CH:23]=2)=[CH:14][CH:13]=1)([O-:11])=[O:10].Cl[CH2:25][CH2:26][C@@H:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[C:37]([O:43][CH3:44])[CH:36]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C.O>[CH3:44][O:43][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][C:38]=1[O:41][CH3:42])[O:34][C@@H:27]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:26][CH2:25][N:21]1[CH2:20][CH:19]=[C:18]([C:15]2[CH:16]=[CH:17][C:12]([N+:9]([O-:11])=[O:10])=[CH:13][CH:14]=2)[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 220487834-(4-Nitrophenyl)-1,2,3,6-tetrahydropyridineHCID 600786704-([(1R)-3-chloro-1-phenylpropyl]oxy)-1,2-dimethoxybenzene

Product 1

HCID 695238791-[(3R)-3-(3,4-Dimethoxyphenoxy)-3-phenylpropyl]-4-(4-nitrophenyl)-1,2,3,6-tetrahydropyridineYield 76.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of potassium carbonate (24.0 mg, 0.174 mmol), sodium iodide (39.0 mg, 0.260 mmol), 4-(4-nitrophenyl)-1,2,3,6-tetrahydropyridine (35.4 mg, 0.174 mmol) and 4-{[(1R)-3-chloro-1-phenylpropyl]oxy}-1,2-dimethoxybenzene (53.4 mg, 0.174 mmol) in DMF (0.5 mL) was stirred at 100° C. for 3 hrs, at which time TLC indicated that the reaction was complete. The reaction mixture was poured into water (5.0 mL) and the aqueous layer was extracted with methylene chloride (3×30 mL). The combined organic extracts were washed with brine (30 mL), dried over MgSO4 and concentrated under reduced pressure. The crude product was purified by Prep-TLC plates [1:1=hexane:ethyl acetate with 1% NH3] afforded the product (63.1 mg, 76.6%) as a yellow oil. The product was used in next reaction without further purification.

Workup

  1. extractionthe aqueous layer was extracted with methylene chloride (3×30 mL)
  2. washThe combined organic extracts were washed with brine (30 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by Prep-TLC plates [1:1=hexane:ethyl acetate with 1% NH3]

Sources & evidence

ORD record
ord-c38d4e6af33c403880e76c7e7944dc55
Source dataset
uspto-grants-2006_06
Patent number
US07067534B1

Reaction notes

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