Hydrogen Bromide → 1'-[5-[[3,5-Dichlorophenyl]methoxy]-3-(3,4-dichlorophenyl)-4-oxopentyl]-1,2-dihydro-spiro[3H-indole-3,4'-piperidine]

HRID 1586393Notes

Reaction equation

HRID 1586393 reaction equation
Br.[Cl:2][C:3]1[CH:4]=[C:5]([CH:10]([C:37](=[O:49])[CH2:38][O:39][CH2:40][C:41]2[CH:46]=[C:45]([Cl:47])[CH:44]=[C:43]([Cl:48])[CH:42]=2)[CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][C:16]3([C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20](C(OCC4C=CC=CC=4)=O)[CH2:19]3)[CH2:15][CH2:14]2)[CH:6]=[CH:7][C:8]=1[Cl:9].CCOCC>C(O)(=O)C>[Cl:48][C:43]1[CH:42]=[C:41]([CH2:40][O:39][CH2:38][C:37](=[O:49])[CH:10]([C:5]2[CH:6]=[CH:7][C:8]([Cl:9])=[C:3]([Cl:2])[CH:4]=2)[CH2:11][CH2:12][N:13]2[CH2:14][CH2:15][C:16]3([C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[NH:20][CH2:19]3)[CH2:17][CH2:18]2)[CH:46]=[C:45]([Cl:47])[CH:44]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 21216777HCID 21216777, compound

Product 1

HCID 212167751'-[5-[[3,5-Dichlorophenyl]methoxy]-3-(3,4-dichlorophenyl)-4-oxopentyl]-1,2-dihydro-spiro[3H-indole-3,4'-piperidine]

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Add a solution of HBr (gas) in acetic acid (3.0 ml) to phenylmethyl 1'-[3-(3,4-dichlorophenyl)-5-[(3,5-dichlorophenyl)methoxy]-4-oxopentyl]-1,2-dihydro-spiro[3H-indole-3,4'-piperidine]-1-carboxylate [0.250 g, 0.34 mmoles) dissolved in glacial acetic acid (2.0 ml). Stir the solution at room temperature for 4 h, then add Et2O (30 ml). Decant the liquid and wash the resultant solid with Et2O. Suspend the solid in water (10 ml) and add 1.0M aqueous KOH (5.0 ml). Extract the mixture with Et2O (3×30 ml), combine the extracts, wash with water and dry (Na2SO4). Remove the solvent and purify the reaction mixture by preparative thin layer chromatography (SiO2), eluting the plates twice with ETOAc:hexanes:CH3OH(NH3) (15:85:3). Extract the desired product with 5% CH3OH(NH3)/EtOAc. Yield: 57 mg.

Workup

  1. customDecant the liquid
  2. washwash the resultant solid with Et2O
  3. additionadd 1.0M aqueous KOH (5.0 ml)
  4. extractionExtract the mixture with Et2O (3×30 ml)
  5. washwash with water
  6. dry with materialdry (Na2SO4)
  7. customRemove the solvent
  8. custompurify the reaction mixture by preparative thin layer chromatography (SiO2)
  9. washeluting the plates twice with ETOAc
  10. extractionExtract the desired product with 5% CH3OH(NH3)/EtOAc

Sources & evidence

ORD record
ord-25092b136b2645838297e7b91d3359c1
Source dataset
uspto-grants-1999_08
Patent number
US05945428

Reaction notes

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