HCID 131713386, compound → HCID 20239783, compound

HRID 485780Notes

Reaction equation

HRID 485780 reaction equation
[OH2:1].[N:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][N:4]=[CH:3]1.C1(N)C(F)=C(F)C(F)=C(N)C=1F.[ClH:27].Cl>O>[ClH:27].[ClH:27].[OH2:1].[N:2]1([CH2:7][CH2:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:5][N:4]=[CH:3]1

Participants

3

Reactant 1

HCID 131713386HCID 131713386, compound

Product 1

HCID 20239783HCID 20239783, compoundYield 207.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of imidazole (4.5 g, 65.8 mM) and sodium hydride (50% by weight in mineral oil, 3.15 g, 66 mM) at 50° C. was added 4-(2-bromoethyl)-1-piperidine carboxaldehyde (12 g, 55 mM) and the reaction was heated at 50° C. for 3 hrs. The solvent was removed in vacuo and water (about 100 ml) was added to the residue and then the mixture was extracted with methylene chloride (3×100 ml). The combined extracts, dried over Na2SO4, were stripped to dryness and purified on silica gel columns, eluted with methanol-methylene chloride (1:9 parts by volume) to give an oil (10.4 g) which was then refluxed with 2N hydrochloric acid (55 ml) in dioxane (400 ml) for 5 hrs. The solvent was removed and the product was crystallized from ethanol diethyl ether yield 4-[2-(1H-imidaz-1-yl)ethyl]piperidine-hydrate-dihydrochloride in overall yield of 55%. 8.2 g of 4-[2-(1H-imidaz-1-yl)ethyl]piperidine-hydrate-dihydrochloride was converted to free base by dissolving in water (100 ml) at pH 11 and extracting with methylene chloride. Evaporation of the methylene chloride extracts in vacuo gave 5.1 g of free base.

Workup

  1. extractionextracting with methylene chloride
  2. customEvaporation of the methylene chloride

Sources & evidence

ORD record
ord-5a4d2991f13444d5b82dacef7310e20e
Source dataset
uspto-grants-1985_08
Patent number
US04537969

Reaction notes

Loading…