Methanol → HCID 86734881, compound

HRID 437632Notes

Reaction equation

HRID 437632 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[C:5]([N:7]1[CH2:9][CH2:8]1)=[O:6].[NH:14]1[CH2:19][CH2:18][CH:17]([N:20]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[NH:22][C:21]2=[O:29])[CH2:16][CH2:15]1.CO.[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34]>CC(=O)C.C1C=CC=CC=1>[C:32]([OH:37])(=[O:36])[C:33]([OH:35])=[O:34].[O:29]=[C:21]1[N:20]([CH:17]2[CH2:16][CH2:15][N:14]([CH2:8][CH2:9][NH:7][C:5](=[O:6])[C:4]3[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=3[O:2][CH3:1])[CH2:19][CH2:18]2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[NH:22]1

Participants

7

Reactant 4

HCID 887MethanolHCID 971Oxalic AcidHCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 21428987HCID 21428987, compound

Product 1

HCID 86734881HCID 86734881, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 241BenzeneSolvent

Procedure

A mixture of 1.75 parts of 1-(2-methoxy-benzoyl)aziridine, 2.18 parts of 1,3-dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one, 1.6 parts of methanol and 10.8 parts of benzene is stirred and refluxed for 1.50 hours. The reaction mixture is cooled. After the addition of 2-propanone, the whole is acidified with ethanedioic acid. The formed ethanedioate salt is filtered off and crystallized from ethanol 70%, yielding 2.9 parts of N-{2-[4-(2,3-dihydro-2-oxo-1 H-benzimidazol-1-yl)-1-piperidinyl] ethyl}-2-methoxybenzamide ethanedioate; mp. 217.4° C.

Workup

  1. temperaturerefluxed for 1.50 hours
  2. temperatureThe reaction mixture is cooled
  3. filtrationThe formed ethanedioate salt is filtered off
  4. customcrystallized from ethanol 70%

Sources & evidence

ORD record
ord-18bb0b82316341e0838e7b33f1c98bfa
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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