Sodium Iodide → HCID 86748649, compound

HRID 1655015Notes

Reaction equation

HRID 1655015 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O[C:18]1(C2C=CC(OC)=C(OC)C=2)C[CH2:22][NH:21][CH2:20][CH2:19]1.C1(C)C=CC(S(O)(=O)=[O:41])=CC=1.ClCCCNC([N:52]1[CH2:56][CH2:55][CH2:54][C:53]1=[O:57])=O.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH2:16][CH2:15][N:14]([N:21]([CH2:20][CH2:19][CH3:18])[C:22]([CH:54]3[CH2:55][CH2:56][NH:52][C:53]3=[O:57])=[O:41])[CH2:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

9

Reactant 6

HCID 5238Sodium IodideHCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 61299094427-39-1HCID 14441092HCID 14441092, compoundHCID 150347144-(3,4-Dimethoxyphenyl)piperidin-4-ol

Product 1

HCID 86748649HCID 86748649, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3.76 g of 4-(3,4-dimethoxyphenyl)-1,2,5, 6-tetrahydropyridine (V-7), which was prepared by the reaction of 4-hydroxy-4-(3,4-dimethoxyphenyl)piperidine and p-toluenesulfonic acid, and 2.94 g of 1-(3-chloropropylcarbamoyl)-2-oxopyrrolidine in 35 ml of DMF is added 3.98 g of K2CO3 and 3.22 g of NaI. The reaction mixture is stirred at 100°-105° C. for 6 days under nitrogen gas. After cooling to room temperature, the mixture is diluted with ethyl acetate, washed with brine and dried over MgSO4. After removal of the solvent, the residue is subjected to column chromatography with silica gel, eluting with CH2Cl2 /MeOH (20/1) to prepare 1.78 g (Yield: 33.4%) of the compound (I a-105) as solid. The oxalate is recrystallized from iPrOH-MeOH to prepare needles. mp. 178.0°-182.0° C.

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customAfter removal of the solvent
  4. washeluting with CH2Cl2 /MeOH (20/1)

Sources & evidence

ORD record
ord-8454f2b4333948a2ab8b49bae6994e04
Source dataset
uspto-grants-1995_04
Patent number
US05410058

Reaction notes

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