p-Toluenesulfonic acid monohydrate → HCID 12017138, compound

HRID 1016431Notes

Reaction equation

HRID 1016431 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][CH2:10][C:11]1[N:15]([CH2:16][CH2:17][C:18]#[N:19])[C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=2[N:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][CH2:8][CH2:9][CH2:10][C:11]1[N:15]([CH2:16][CH2:17][C:18]#[N:19])[C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]=2[N:12]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12017137HCID 12017137, compound

Product 1

HCID 12017138HCID 12017138, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The crude 3-{2-[3-(tetrahydro-pyran-2-yloxy)-propyl]-benzimidazol-1-yl }-propionitrile was stirred in 250 mL of methanol with sufficient p-toluenesulfonic acid monohydrate to make the solution acidic (pH=1-2). After stirring overnight, the solution was concentrated under reduced pressure, made basic (pH=8) with 1N sodium hydroxide and extracted into 8×50 mL of ethyl acetate. The aqueous layer was saturated with NaCl to aid in extraction of the product. The combined extracts were dried over magnesium sulfate and concentrated under reduced pressure. Chromatography using a gradient of ethyl acetate then 10% methanol in ethyl acetate followed by trituration with ether-hexane gave 4.8 g of 3-[2-(3-hydroxy-propyl)-benzimidazol-1-yl]-propionitrile as a solid.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. extractionextracted into 8×50 mL of ethyl acetate
  3. extractionto aid in extraction of the product
  4. dry with materialThe combined extracts were dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8186b9be4c474b5596b97f5c19422e04
Source dataset
uspto-grants-2002_11
Patent number
US06476041B1

Reaction notes

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