Hydrochloric Acid → HCID 18922047, compound

HRID 1289815Notes

Reaction equation

HRID 1289815 reaction equation
C[Al](C)C.Cl.Cl.[NH2:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:14]=[CH:15][CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:10][CH2:9]1.[CH:20]1([C:25]([OH:37])([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][N:32]=2)[C:26](OCC)=[O:27])[CH2:24][CH2:23][CH2:22][CH2:21]1.Cl.C(=O)(O)[O-].[Na+]>CCCCCC.C1(C)C=CC=CC=1>[CH3:18][C:17]([CH3:19])=[CH:16][CH2:15][CH2:14][N:11]1[CH2:12][CH2:13][CH:8]([NH:7][C:26](=[O:27])[C:25]([CH:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)([OH:37])[C:31]2[CH:36]=[CH:35][N:34]=[CH:33][N:32]=2)[CH2:9][CH2:10]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 16682925TrimethylaluminumHCID 18922145HCID 18922145, compoundHCID 73471138HCID 73471138, compound

Product 1

HCID 18922047HCID 18922047, compoundYield 13.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

0.65 ml of a 1M trimethylaluminum solution in hexane was added to a solution of 85 mg of 4-amino-1-(4-methyl-pentenyl)piperidine dihydrochloride in 5 ml of toluene under cooling with ice, and this mixture was stirred at the same temperature for 2 hours. A solution of 29 mg of ethyl 2-cyclopentyl-2-hydroxy-2-(4-pyrimidinyl)acetate in 3 ml of toluene was added to the reaction mixture. The resulting mixture was stirred at 100° C. for 18 hours, mixed with 1N hydrochloric acid under cooling with ice, made alkaline with a saturated aqueous solution of sodium bicarbonate, and extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous magnesium sulfate. After the solvent was distilled off, the resulting residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. 35 Merck); developing solvent: chloroform/methanol=9/1] to obtain 6 mg of the title compound.

Workup

  1. temperatureunder cooling with ice
  2. stirringThe resulting mixture was stirred at 100° C. for 18 hours
  3. temperatureunder cooling with ice
  4. extractionextracted with chloroform
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe resulting residue was purified by preparative thin layer chromatography [Kieselgel™ 60F254, Art 5744 (manufactured by E. 35 Merck); developing solvent: chloroform/methanol=9/1]

Sources & evidence

ORD record
ord-995a5f0732ea40baae1caadd45732100
Source dataset
uspto-grants-1998_05
Patent number
US05750540

Reaction notes

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