Hydrogen chloride-ethyl acetate → 2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine

HRID 2383019Notes

Reaction equation

C(OC(=O)[NH:7][CH2:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]1[CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:10])(C)(C)C.Cl.CCOC(C)=O>CCOC(C)=O>[CH:21]1([CH:12]2[C:13]3[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:19][CH2:20][N:11]2[C:9](=[O:10])[CH2:8][NH2:7])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

Conditions

Temperature: 50 °C

Procedure

Tert-butyl[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]carbamate (1.5 g) was dissolved in EtOAc (20 mL), and 4 M HCl/EtOAc (3 mL) was added thereto under ice-cooling, followed by stirring at 50° C. for 5 hours. Then, the reaction solvent was evaporated. Saturated aqueous sodium bicarbonate was added to the reaction liquid which was then extracted with chloroform. The extract was washed with saturated brine and dried over magnesium sulfate. The solvent was evaporated and the resulting residue was purified by silica gel column chromatography (chloroform-MeOH) to obtain 2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethanamine (1.09 g).

Workup

temperatureunder ice-cooling
customThen, the reaction solvent was evaporated
additionSaturated aqueous sodium bicarbonate was added to the reaction liquid which
extractionwas then extracted with chloroform
washThe extract was washed with saturated brine
dry with materialdried over magnesium sulfate
customThe solvent was evaporated
customthe resulting residue was purified by silica gel column chromatography (chloroform-MeOH)

Sources & evidence

ORD record: ord-7a20500d789c4f14b5e2b2c6c8b218b9
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08263607B2

Reaction notes

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