Sodium Hydroxide → 3-{3-[4-(diphenylmethyl)-1-piperazinyl]-propyl}-2,3-dihydro-2-oxo-1H-benzimidazole-1-acetic acid hemihydrate

HRID 355005

Reaction equation

HRID 355005 reaction equation
[C:1]1([CH:7]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([CH2:26][C:27]([O:29]CC)=[O:28])[C:18]3=[O:32])[CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+]>O>[OH2:28].[C:33]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([CH2:26][C:27]([OH:29])=[O:28])[C:18]3=[O:32])[CH2:12][CH2:13]2)[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1.[C:1]1([CH:7]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][N:17]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[N:19]([CH2:26][C:27]([OH:29])=[O:28])[C:18]3=[O:32])[CH2:10][CH2:9]2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20506279ethyl 3-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-2,3-dihydro-2-oxo-1H-benzimidazole-1-acetate

Product 1

HCID 887389743-{3-[4-(diphenylmethyl)-1-piperazinyl]-propyl}-2,3-dihydro-2-oxo-1H-benzimidazole-1-acetic acid hemihydrate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 9.8 parts of ethyl 3-{3 -[4-(diphenylmethyl)1-piperazinyl]propyl}-2,3-dihydro-2-oxo-1H-benzimidazole-1-acetate, 1.2 parts of sodium hydroxide and 150 parts of water is stirred and refluxed for 5 minutes (+80° C.). The reaction mixture is filtered and the filtrate is acidified with acetic acid to pH 5.8-6: a sticky precipitate is formed. It is separated and crystallized from ethanol and water. The product is filtered off and dried in vacuo at 100° C. for 3 hours, yielding 6 parts of 3-{3-[4-(diphenylmethyl)-1-piperazinyl]propyl}-2,3-dihydro-2-oxo-1H-benzimidazole-1-acetic acid hemihydrate; mp. 138.7° C.

Workup

  1. temperaturerefluxed for 5 minutes (+80° C.)
  2. filtrationThe reaction mixture is filtered
  3. customa sticky precipitate is formed
  4. customIt is separated
  5. customcrystallized from ethanol and water
  6. filtrationThe product is filtered off
  7. customdried in vacuo at 100° C. for 3 hours

Sources & evidence

ORD record
ord-ce735da5251d401d9bd5872a61d3f2d3
Source dataset
uspto-grants-1983_03
Patent number
US04377578

Linked notes

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