Hydrochloric Acid → HCID 178478581, compound

HRID 1262416Notes

Reaction equation

HRID 1262416 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]2[NH:8][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]3)=[N:10][C:6]=2[CH:5]=1)([O-])=O.[ClH:23]>CO.[Pt]>[ClH:23].[ClH:23].[ClH:23].[ClH:23].[NH2:1][C:4]1[CH:22]=[CH:21][C:7]2[NH:8][C:9]([CH2:11][N:12]3[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][OH:20])[CH2:14][CH2:13]3)=[N:10][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 178526484HCID 178526484, compound

Product 1

HCID 178478581HCID 178478581, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 887MethanolSolvent4×

Procedure

2-[4-(5-Nitro-1H-benzimidazol-2-ylmethyl)-piperazin-1-yl]-ethanol (1.085 g, 2.587 mmol) [Goker, H.; Kus, C.; Abbasoglu, U. Arch. Pharm. (Weinheim, Ger.) 1995, 328, 425]was dissolved in Methanol (20.0 mL) and 5% Platinum on Carbon, Sulfided (0.5%) (162 mg, 0.0415 mmol) and 3.00 M of Hydrogen Chloride in Methanol (8.0 mL, 24 mmol) were added. The mixture was shaken under an atmosphere of Hydrogen (25 psi) for 2 h. The mixture was filtered through Celite with MeOH and additional 3.00 M of Hydrogen Chloride in Methanol (3 mL, 9 mmol) was added to the filtrate prior to conc. in vacuo to afford 2-[4-(5-Amino-1H-benzimidazol-2-ylmethyl)-piperazin-1-yl]-ethanol tetrahydrochloride as a foam (0.90 g, 83%). 1H-NMR (DMSO-d6): 10.41 (br s, 1H), 7.72 (d, 1H, J=8.6 Hz), 7.52 (s, 1H), 7.25 (d, 1H, J=8.6 Hz), 4.20 (s, 2H), 3.78 (t, 2H, J=4.8 Hz), 3.53 (m, 2H), 3.19 (m, 4H), 3.09 (m, 2H), 2.85 (m, 2H).

Workup

  1. additionwas added to the filtrate

Sources & evidence

ORD record
ord-c331a211304048ddbf432f7625a5dacd
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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