Hydrochloric Acid → HCID 57571690, compound

HRID 1677103Notes

Reaction equation

HRID 1677103 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20](=[O:30])[NH:21][CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26]C=3)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CO.C(Cl)Cl>[CH2:22]([NH:21][C:20](=[O:30])[C:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[N:15][CH:16]=1)[C:23]1[CH:24]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66995381HCID 66995381, compound

Product 1

HCID 57571690HCID 57571690, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(5-phenethylcarbamoyl-pyridin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (200 mg) in MeOH (5 ml) was cooled to 0° C. and slowly treated with 4N HCl (2.52 ml). The reaction mixture was stirred at r.t. overnight, then diluted with CH2Cl2 and directly purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; gradient: CH2Cl2→CH2Cl2/MeOH 9:1) to give N-benzyl-6-piperazin-1-yl-nicotinamide as off-white solid. MS (ISP): 297.5 ([M+H]+)

Workup

  1. customdirectly purified by column chromatography (Isolute® SPE flash NH2 column, aminopropyl-functionalized silica; gradient: CH2Cl2→CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-3075d74d98194db081d93bdad47c8aa3
Source dataset
uspto-grants-2011_08
Patent number
US08008305B2

Reaction notes

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