(1-methyl-1H-indol-3-yl)(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-6-yl)methanone → (R)-(-)-5-[(1-methylindol-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole (+)-dibenzoyltartarate

HRID 2225617Notes

Reaction equation

HRID 2225617 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([CH:13]2[CH2:21][CH2:20][C:16]3[N:17]=[CH:18][NH:19][C:15]=3[CH2:14]2)=[O:12])=[CH:3]1.[C:22]([C:30]([C:45]([OH:47])=[O:46])([OH:44])[C:31]([C:36](=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([OH:35])[C:32]([OH:34])=[O:33])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[C:36]([C:31]([C:32]([OH:34])=[O:33])([OH:35])[C:30]([C:22](=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([OH:44])[C:45]([OH:47])=[O:46])(=[O:43])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([C@@H:13]2[CH2:21][CH2:20][C:16]3[N:17]=[CH:18][NH:19][C:15]=3[CH2:14]2)=[O:12])=[CH:3]1

Participants

4

Reactant 2

HCID 4442(1-methyl-1H-indol-3-yl)(4,5,6,7-tetrahydro-1H-benzo[d]imidazol-6-yl)methanoneHCID 12362975HCID 12362975, compound

Product 1

HCID 131718657(R)-(-)-5-[(1-methylindol-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole (+)-dibenzoyltartarateYield 17.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In 60 ml of methanol was added 5.87 g of 5-[(1-methylindol-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole obtained in Example 41, and a solution of 7.52 g of (+)-dibenzoyltartaric acid in 240 ml of methanol was added thereto to once form a clear solution. On leaving the solution to stand at room temperature for one night, there were precipitated crystals, which were collected by filtration and recrystallized three times from dimethylformamide/water to obtain 2.30 g of (R)-(-)-5-[(1-methylindol-3-yl)carbonyl]-4,5,6,7-tetrahydrobenzimidazole (+)-dibenzoyltartarate.

Workup

  1. customto once form a clear solution
  2. customOn leaving the solution
  3. waitto stand at room temperature for one night
  4. customthere were precipitated crystals, which
  5. filtrationwere collected by filtration
  6. customrecrystallized three times from dimethylformamide/water

Sources & evidence

ORD record
ord-43667c6107674878abfd04afc35f83d8
Source dataset
uspto-grants-1994_09
Patent number
US05344927

Reaction notes

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