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1-[2-[4-(2-Methoxycarbonyl-2-methylpropyl)phenyl]ethyl]-1,5-diazacyclooctane → 1-[1-(4-chlorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonyl-2-methylpropyl)phenyl]ethyl]-1,5-diazacyclooctane

HRID 55331
Notes
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Reaction equation

HRID 55331 reaction equation
Br[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][CH:9]=2)[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.[CH3:19][O:20][C:21]([C:23]([CH3:42])([CH3:41])[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH2:32][N:33]2[CH2:40][CH2:39][CH2:38][NH:37][CH2:36][CH2:35][CH2:34]2)=[CH:27][CH:26]=1)=[O:22]>C(O)CCC>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][N:6]2[C:5]3[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=3[N:3]=[C:2]2[N:37]2[CH2:38][CH2:39][CH2:40][N:33]([CH2:32][CH2:31][C:28]3[CH:29]=[CH:30][C:25]([CH2:24][C:23]([C:21]([O:20][CH3:19])=[O:22])([CH3:42])[CH3:41])=[CH:26][CH:27]=3)[CH2:34][CH2:35][CH2:36]2)=[CH:9][CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 199575131-[2-[4-(2-Methoxycarbonyl-2-methylpropyl)phenyl]ethyl]-1,5-diazacyclooctaneHCID 199575172-bromo-1-(4-chlorophenylmethyl)-1H-benzimidazole

Product 1

HCID 199575141-[1-(4-chlorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonyl-2-methylpropyl)phenyl]ethyl]-1,5-diazacyclooctaneYield 58%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 2-bromo-1-(4-chlorophenylmethyl)-1H-benzimidazole (0.029 g) in n-butanol (0.5 ml) was added 1-[2-[4-(2-methoxycarbonyl-2-methylpropyl)phenyl]ethyl]-1,5-diazacyclooctane (0.102 g), and the mixture was refluxed for 3 hours. The reaction mixture was quenched with a saturated aqueous NaHCO3 solution (30 ml), and the mixture was extracted with methylene chloride (20 ml). The extract was washed with water, and dried over anhydrous MgSO4. The solvent was removed under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on a silica gel column using a mixture of methylene chloride, diethyl ether and methanol (1:1:0.2) as eluent to give 1-[1-(4-chlorophenylmethyl)-1H-benzimidazol-2-yl]-5-[2-[4-(2-methoxycarbonyl-2-methylpropyl)phenyl]ethyl]-1,5-diazacyclooctane (0.030 g) as a colorless oily liquid.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe reaction mixture was quenched with a saturated aqueous NaHCO3 solution (30 ml)
  3. extractionthe mixture was extracted with methylene chloride (20 ml)
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was purified by medium pressure liquid column chromatography on a silica gel column
  8. additiona mixture of methylene chloride, diethyl ether and methanol (1:1:0.2) as eluent

Sources & evidence

ORD record
ord-e73b6b9de0744504bd3c6e59ec7f1560
Source dataset
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05624948

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes