Sodium Iodide → HCID 15595024, compound

HRID 2118677Notes

Reaction equation

HRID 2118677 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)([OH:15])[CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][CH2:26][N:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[NH:29][C:28]1=[O:36].C([O-])([O-])=O.[Na+].[Na+].[Na+].[I-]>C(C(C)=O)C(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=2)([OH:15])[CH:9]2[CH2:10][CH2:11][N:12]([CH2:24][CH2:25][CH2:26][N:27]3[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[NH:29][C:28]3=[O:36])[CH2:13][CH2:14]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 11208889Bis(4-fluorophenyl)(piperidin-4-yl)methanolHCID 135640291-(3-BroMopropyl)-1,3-dihydro-2H-benziMidazol-2-one

Product 1

HCID 15595024HCID 15595024, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

2.1 g (0.007 mole) of 4-[bis(4-fluorophenyl)hydroxymethyl]piperidine, 1.8 g (0.007 mole) of 1-(1-bromo-3-propyl)-1,3-dihydro-2(2H)-benzimidazolone, 0.85 g (0.008 mole) of Na2CO3 and a few crystals of NaI are heated for 5 h at reflux temperature in 60 ml of methyl isobutyl ketone. The solvent is evaporated off, the residue is taken up with a mixture of water and CH2Cl2, and the organic phase is dried and evaporated down. A solid residue is obtained which is chromatographed on a column of silica (eluent: CH2Cl2/MeOH 97/3, 96/4 and then 94/6). The pure fractions are evaporated down, the evaporation residue is taken up with ether and a white product is filtered off and crystallized from 90 ml of ethyl acetate. M.p.=141°-143° C.

Workup

  1. customThe solvent is evaporated off
  2. additionthe residue is taken up with a mixture of water and CH2Cl2
  3. customthe organic phase is dried
  4. customevaporated down
  5. customA solid residue is obtained which
  6. customis chromatographed on a column of silica (eluent
  7. customThe pure fractions are evaporated down
  8. filtrationa white product is filtered off
  9. customcrystallized from 90 ml of ethyl acetate

Sources & evidence

ORD record
ord-0826a1cd8ad34941ac8afa86948354f6
Source dataset
uspto-grants-1987_07
Patent number
US04680296

Reaction notes

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