4-Oxiranylmethoxy-1,3-dihydro-2-benzimidazolone → 1-[N-benzyl-N-(6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl) amino]-3-(1,3-dihydro-2-benzoimidazolon-4-yloxy)-2-propanol

HRID 2299658Notes

Reaction equation

HRID 2299658 reaction equation
[O:1]1[CH2:3][CH:2]1[CH2:4][O:5][C:6]1[C:14]2[NH:13][C:12](=[O:15])[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH2:16]([NH:23][CH:24]1[CH2:30][CH2:29][CH2:28][C:27]2[CH:31]=[C:32]([OH:35])[CH:33]=[CH:34][C:26]=2[CH2:25]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:16]([N:23]([CH2:3][CH:2]([OH:1])[CH2:4][O:5][C:6]1[C:14]2[NH:13][C:12](=[O:15])[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH:24]1[CH2:30][CH2:29][CH2:28][C:27]2[CH:31]=[C:32]([OH:35])[CH:33]=[CH:34][C:26]=2[CH2:25]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 129015214-Oxiranylmethoxy-1,3-dihydro-2-benzimidazoloneHCID 18007216N-benzyl-(6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl)amine

Product 1

HCID 98910181-[N-benzyl-N-(6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl) amino]-3-(1,3-dihydro-2-benzoimidazolon-4-yloxy)-2-propanolYield 64.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-oxiranylmethoxy-1,3-dihydro-2-benzimidazolone (82.5 mg) and N-benzyl-(6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl)amine (107 mg) in ethanol (1.5 ml) was stirred under reflux for 13 hours, cooled to room temperature and evaporated in vacuo. The residue was chromatographed (dichloromethane-methanol)by silica gel (4.2 g) to afford 1-[N-benzyl-N-(6,7,8,9-tetrahydro-2-hydroxy-5H-benzocyclohepten-6-yl) amino]-3-(1,3-dihydro-2-benzoimidazolon-4-yloxy)-2-propanol (123 mg) as a colorless powder.

Workup

  1. temperatureunder reflux for 13 hours
  2. customevaporated in vacuo
  3. customThe residue was chromatographed (dichloromethane-methanol)by silica gel (4.2 g)

Sources & evidence

ORD record
ord-58618ebe910f415c9b7949cc4d304589
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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