Sodium Iodide → HCID 86606832, compound

HRID 1437682Notes

Reaction equation

HRID 1437682 reaction equation
Cl.[F:2][C:3]([F:29])([F:28])[C:4]1[CH:5]=[C:6]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:7][O:8][C@H:9]1[CH2:14][CH2:13][NH:12][CH2:11][C@H:10]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(C(C)C)CC)(C)C.[Cl:39][CH2:40][C:41](Cl)=[O:42].[I-].[Na+].[C:46]([N:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1)(=[O:48])[CH3:47]>CN(C=O)C.O>[ClH:39].[C:46]([N:49]1[CH2:54][CH2:53][N:52]([CH2:40][C:41]([N:12]2[CH2:13][CH2:14][C@H:9]([O:8][CH2:7][C:6]3[CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[CH:23]=[C:4]([C:3]([F:2])([F:28])[F:29])[CH:5]=3)[C@H:10]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:11]2)=[O:42])[CH2:51][CH2:50]1)(=[O:48])[CH3:47]

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 6577Chloroacetyl chlorideHCID 81531Diisopropylethylamine2×HCID 837951-AcetylpiperazineHCID 86606807cis-4-[[3,5-Bis(trifluoromethyl)benzyl]oxy]-3-phenylpiperidine hydrochloride

Product 1

HCID 86606832HCID 86606832, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound (175 mg) obtained in Example 1 and diisopropylethylamine (113 mg) in DMF (5 ml), chloroacetyl chloride (50 mg) was added at room temperature, and the reaction mixture was stirred for 1 hour. To the reaction solution, diisopropylethylamine (113 mg), sodium iodide (180 mg) and 1-acetylpiperazine (102 mg) were added and the reaction mixture was further stirred for 5 hours. To the reaction solution, water was added, and the product was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried, and then the solvent was evaporated under reduced pressure. The obtained residue was treated with 4 N hydrogen chloride/ethyl acetate to obtain the title compound (150 mg) as colorless powder.

Workup

  1. stirringthe reaction mixture was further stirred for 5 hours
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. additionThe obtained residue was treated with 4 N hydrogen chloride/ethyl acetate

Sources & evidence

ORD record
ord-1cea730ce49c4cce8b749e3e4f76829f
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

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