Hydrochloric Acid → HCID 46832949, compound

HRID 1622909Notes

Reaction equation

HRID 1622909 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[CH2:15][CH2:14][N:13]([CH:16]([CH3:29])[C:17]([C:19]2[CH:28]=[CH:27][C:22]3[NH:23][C:24](=[O:26])[NH:25][C:21]=3[CH:20]=2)=[O:18])[CH2:12][CH2:11]1.[BH4-].[Na+].Cl>CO>[OH:18][CH:17]([C:19]1[CH:28]=[CH:27][C:22]2[NH:23][C:24](=[O:26])[NH:25][C:21]=2[CH:20]=1)[CH:16]([N:13]1[CH2:14][CH2:15][N:10]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[O:3][CH3:2])[CH2:11][CH2:12]1)[CH3:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 67999698HCID 67999698, compound

Product 1

HCID 46832949HCID 46832949, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 5-(2-(4-(2-methoxyphenyl)piperazin-1-yl)propanoyl)-1H-benzo[d]imidazol-2(3H)-one hydrochloride (1.67 g, 4 mmol) was dissolved in 50 ml of methanol solution, and sodium borohydride (0.15 g, 8.4 mmol) was added in proportions, mixed and stirred at room temperature for 3 hours. Working up according to general procedure B gave 0.57 g of (1RS, 2SR)-5-(1-hydroxy-2-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-1H-benzo[d]imidazol-2(3H)-one (IV-3) hydrochloride having a melting point of 221 to 223° C., with a yield of 34.0%; and 0.50 g of (1RS,2RS)-5-(1-hydroxy-2-(4-(2-methoxyphenyl)piperazin-1-yl)propyl)-1H-benzo[d]imidazol-2(3H)-one (IV-4) hydrochloride having a melting point of 242 to 244° C., with a yield of 29.8%.

Workup

  1. additionmixed

Sources & evidence

ORD record
ord-21b5e3b547d54cba95e0012eb3eba144
Source dataset
uspto-grants-2014_07
Patent number
US08778948B2

Reaction notes

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