Sodium Iodide → HCID 86606834, compound

HRID 1437683Notes

Reaction equation

HRID 1437683 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Cl:19][CH2:20][C:21](Cl)=[O:22].[I-].[Na+].Cl.[F:27][C:28]([F:54])([F:53])[C:29]1[CH:30]=[C:31]([CH:46]=[C:47]([C:49]([F:52])([F:51])[F:50])[CH:48]=1)[CH2:32][O:33][C@H:34]1[CH2:39][CH2:38][NH:37][CH2:36][C@H:35]1[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1>CN(C=O)C.O>[ClH:19].[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:21](=[O:22])[CH2:20][N:37]2[CH2:38][CH2:39][C@H:34]([O:33][CH2:32][C:31]3[CH:46]=[C:47]([C:49]([F:51])([F:52])[F:50])[CH:48]=[C:29]([C:28]([F:27])([F:53])[F:54])[CH:30]=3)[C@H:35]([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[CH2:36]2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

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 86606834HCID 86606834, compoundYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-acetylpiperazine (38 mg) and diisopropylethylamine (45 mg) in DMF (5 ml), chloroacetyl chloride (34 mg) was added at room temperature, and the reaction mixture was stirred for 30 minutes. To the reaction solution, diisopropyethylamine (90 mg), sodium iodide (103 mg) and the compound (100 mg) obtained in Example 1 were added and the reaction mixture was further stirred for 4 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 (96 mg) as pale brown powder.

Workup

  1. stirringthe reaction mixture was further stirred for 4 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-71b314509f4b4919b0034c59ad9194e1
Source dataset
uspto-grants-2009_11
Patent number
US07622487B2

Reaction notes

Loading…