Hydrochloric Acid → HCID 67004412, compound

HRID 1513952Notes

Reaction equation

HRID 1513952 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19]C)[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22].Cl.B(Br)(Br)Br.C(=O)(O)[O-].[Na+]>CCOCC.C(Cl)(Cl)Cl.C(O)(C)C.C(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:19])[CH:15]=2)[C:10]=1[C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:25][CH:24]=1)=[O:22]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57552522HCID 57552522, compound

Product 1

HCID 67004412HCID 67004412, compoundYield 32%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Charge a flask with [2-(2,3-difluoro-phenyl)-6-methoxy-naphthalen-1-yl]-[4-(2-piperidin-1-yl-ethoxy)-phenyl]-methanone (1.3 g, 2.6 mmol) and add 200 mL methylene chloride followed by 25 mL of HCl in ether (1 M) and evaporate to dryness. Dissolve the solid in 200 mL methylene chloride and chill the solution in ice. Add to this solution boron tribromide (4.0 mL, 42.4 mmol) with swirling. Stir the dark solution at room temperature for 1 hour at which point all the starting material is gone. Pour this into a two phase mixture consisting of saturated sodium bicarbonate aqueous phase and a 3/1 mixture of chloroform/isopropanol organic phase and extract using a separatory funnel. Separate the organic phase and dry over 3 Å molecular sieves. Purify on a silica column eluting with 0-10% methanol/methylene chloride, collecting the first fraction that contains the product to give 400 mg of the title compound (32%).

Workup

  1. customevaporate to dryness
  2. dissolutionDissolve the solid in 200 mL methylene chloride
  3. temperaturechill the solution in ice
  4. additionPour this into a two phase mixture
  5. extractionextract
  6. customSeparate the organic phase
  7. customdry over 3 Å molecular sieves
  8. customPurify on a silica column
  9. washeluting with 0-10% methanol/methylene chloride
  10. customcollecting the first fraction that

Sources & evidence

ORD record
ord-4d87640cbaa846cd9b45224cd5ce83ff
Source dataset
uspto-grants-2012_07
Patent number
US08217032B2

Reaction notes

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