Potassium Carbonate → HCID 64366284, compound

HRID 2411231Notes

Reaction equation

HRID 2411231 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][C:15]=2[CH3:22])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)(Cl)Cl>[CH3:22][C:15]1[CH:16]=[C:17]([CH2:20][OH:21])[CH:18]=[CH:19][C:14]=1[N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21866389Hydrogen chloride-ethyl acetateHCID 71252146HCID 71252146, compound

Product 1

HCID 64366284HCID 64366284, compoundYield 134.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The intermediate 4-(4-methoxycarbonyl-2-methylphenyl)piperazine-1-carboxylic acid tert-butyl ester (1.42 g) described in Preparation Example 97 was dissolved in diethyl ether (18 mL), 0.99M diisobutylaluminum hydride (9 mL) was added under cooling to −78° C., and the mixture was stirred while rising the temperature to room temperature. The mixture was further stirred at room temperature for 2 hr, methanol (0.7 mL) was added, and aqueous solution (5 mL) of Rochelle salt was added. The precipitate was collected by filtration from the reaction mixture, and the filtrate was concentrated. The obtained residue was purified by column chromatography (ethyl acetate:hexane) to give 4-(4-hydroxymethyl-2-methylphenyl)piperazine-1-carboxylic acid tert-butyl ester (720 mg). The obtained 4-(4-hydroxymethyl-2-methylphenyl)piperazine-1-carboxylic acid tert-butyl ester (720 mg) was dissolved in chloroform (6 mL), 4N hydrogen chloride/ethyl acetate solution (2.3 mL) was added, and the mixture was stirred at room temperature overnight. The reaction mixture was neutralized with aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate. The solvent was evaporated from the organic layer to give the title compound (654 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customThe solvent was evaporated from the organic layer

Sources & evidence

ORD record
ord-5556a2c476ac42e8a908facd50659088
Source dataset
uspto-grants-2014_08
Patent number
US08816079B2

Reaction notes

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