1,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-one → HCID 20342592, compound

HRID 2050370Notes

Reaction equation

HRID 2050370 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]([OH:29])[CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[O:28])[CH2:15][CH2:14]2)=[CH:7][C:3]=1[C:4]([OH:6])=O.O[C:31]1[CH:39]=[CH:38][C:37]([C:40](=O)[CH2:41]Br)=[CH:36][C:32]=1C(O)=O.O=C1N(C2CCNCC2)[C:48]2[CH:56]=[CH:57]C=C[C:47]=2[NH:46]1.OC1C=CC(C(=O)CN2CCC(N3C4C=CC=CC=4NC3=O)CC2)=CC=1C(O)=O>>[OH:1][C:2]1[CH:10]=[CH:9][C:8]([CH:11]([OH:29])[CH2:12][N:13]2[CH2:14][CH:15]=[C:16]([N:19]3[C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=4[NH:21][C:20]3=[O:28])[CH2:17][CH2:18]2)=[CH:7][C:3]=1[C:4]([NH:46][CH2:47][CH2:48][CH2:56][CH2:57][CH2:41][CH2:40][CH2:37][CH2:38][CH2:39][CH2:31][CH2:32][CH3:36])=[O:6]

Participants

5

Reactant 4

HCID 886381,3-Dihydro-1-(4-piperidinyl)-2H-benzimidazol-2-oneHCID 2554785-(Bromoacetyl)-2-hydroxybenzoic acidHCID 20342591HCID 20342591, compoundHCID 20342596HCID 20342596, compound3×

Product 1

HCID 20342592HCID 20342592, compound

Procedure

The 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]benzoic acid derivatives of formula (I) are readily prepared by condensing a derivative of 2-hydroxy-5-(2-bromoacetyl)benzoic acid (II) with a 4-(2-oxo-1-benzimidazolinyl)piperidine (III). The resulting 2-hydroxy-5-[4-(2-oxo-1-benzimidazolinyl)piperidinoacetyl]benzoic acid derivative (IV) is subsequently reduced to the desired derivative of 2-hydroxy-5-[1-hydroxy-2-[4-(2-oxo-1-benzimidazolinyl)piperidino]ethyl]benzoic acid (I). This process may be schematically illustrated as follows: ##STR2##

Sources & evidence

ORD record
ord-6e78f638e1fe4e37987c2c89691004ba
Source dataset
uspto-grants-1980_04
Patent number
US04200755

Reaction notes

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