Hydrochloric Acid → (E)-N-(5,6-dihydro-7H-cyclopenta[d]pyrimidin-4-yl)-4-[4-(1-benzylpiperidin-4-yl)-2-butenoyl]aniline

HRID 976133Notes

Reaction equation

Cl[C:2]1[C:3]2[CH2:10][CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:11]([N:18]1[CH2:23][CH2:22][CH:21]([CH2:24][CH:25](O)[CH2:26][C:27]([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)=[O:28])[CH2:20][CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.FC(F)(F)C([O-])=O.Cl.C(=O)([O-])O.[Na+]>C(O)C>[N:5]1[C:4]2[CH2:8][CH2:9][CH2:10][C:3]=2[C:2]([NH:33][C:32]2[CH:34]=[CH:35][C:29]([C:27](=[O:28])/[CH:26]=[CH:25]/[CH2:24][CH:21]3[CH2:22][CH2:23][N:18]([CH2:11][C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:19][CH2:20]3)=[CH:30][CH:31]=2)=[N:7][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

30 ml of ethanol and 0.58 g of 4-chloro-5,6-dihydro-7H-cyclopenta[d]pyrimidine were added to 1.21 g of 4-[4-(1-benzylpiperidin-4-yl)-3-hydroxybutanoyl]aniline·trifluoroacetate, 1 ml of an ethanol solution of hydrochloric acid (containing 0.29 g of hydrochloric acid) was added thereto and the mixture was stirred under heating at 60° C. for 40 minutes. Then, a saturated sodium hydrogen carbonate aqueous solution was added thereto and the mixture was extracted with chloroform. After drying over anhydrous sodium sulfate, the solvent was removed by distillation under reduced pressure and the obtained residue was applied to silica gel column chromatography to obtain 0.40 g of the title compound as yellow powder.

Workup

additionwas added
extractionthe mixture was extracted with chloroform
dry with materialAfter drying over anhydrous sodium sulfate
customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record: ord-85083f227ce645fd875b7f39a556ff66
Source dataset: uspto-grants-1997_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05610303

Reaction notes

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