Ammonia → HCID 22671418, compound

HRID 1006444Notes

Reaction equation

HRID 1006444 reaction equation
[CH2:1]([N:3]([CH2:39][CH3:40])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37]C)[CH:32]=2)[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[NH:23][C:22]3=[O:30])[CH2:17][CH2:16]2)=[CH:8][CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br.CO.N.[Cl:48]CCl>>[ClH:48].[CH2:39]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]([C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[CH:32]=2)[CH2:13][CH2:14][N:15]2[CH2:20][CH2:19][CH:18]([N:21]3[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[NH:23][C:22]3=[O:30])[CH2:17][CH2:16]2)=[CH:10][CH:11]=1)=[O:5])[CH3:40]

Participants

6

Reactant 5

HCID 222AmmoniaHCID 887MethanolHCID 6344Dichloromethane2×HCID 25134Boron tribromideHCID 10187197HCID 10187197, compound

Product 1

HCID 22671418HCID 22671418, compoundYield 85%

Procedure

The 1-[3-(4-diethylcarbamoylphenyl)-3-(3-methoxyphenyl)propyl]-4-(1,3-dihydro-2H-benzimidazol-2-on-1-yl)piperidine (1.196 g) obtained in Example 1 was dissolved in dichloromethane (24 ml), added with a solution of boron tribromide in dichloromethane (1.0 M, 8.8 ml) and stirred at room temperature for 2 hours. The reaction mixture was slowly added with methanol (6 ml) with ice cooling to quench the reaction and then added with 7.5 N aqueous ammonia (40 ml). The layers were separated, and the aqueous layer was extracted with dichloromethane (20 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was dissolved in methanol (24 ml) and added with a solution of hydrochloric acid in methanol (8.8 ml), and then the solvent was evaporated under reduced pressure again. The residue was purified by LH-20 column chromatography (elution solvent: dichloromethane:methanol=1:1) to obtain 1.057 g of the title compound. Yield: 85%.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (20 ml)
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. dissolutionThe residue was dissolved in methanol (24 ml)
  8. additionadded with a solution of hydrochloric acid in methanol (8.8 ml)
  9. customthe solvent was evaporated under reduced pressure again
  10. customThe residue was purified by LH-20 column chromatography (elution solvent: dichloromethane:methanol=1:1)

Sources & evidence

ORD record
ord-6824eaecdb564b5190d2f02d45c32942
Source dataset
uspto-grants-2004_09
Patent number
US06790854B2

Reaction notes

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