4-[3-(3-Methylphenyl)propyl]aniline → HCID 178461175, compound

HRID 330575

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH2:10][C:11]2[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=2)[CH:5]=[CH:6][CH:7]=1>O1CCOCC1.[Ru](=O)=O>[CH3:1][C@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([CH2:8][CH2:9][CH2:10][C@@H:11]2[CH2:12][CH2:13][C@H:14]([NH2:15])[CH2:16][CH2:17]2)[CH2:3]1

Participants

Conditions

Temperature: 140 °C

Procedure

0.5 g of ruthenium dioxide is added to a solution of 63 g (0.28 mole) of 4-[3-(3-methylphenyl)-propyl]aniline in 100 ml of dioxane, and hydrogenation is carried out in a 300 ml stirred autoclave at 140° C. and under an H2 pressure of 300 bar until the pressure remains constant (about 3 hours). The discharged mixture is filtered under suction over kieselguhr, the filtrate is evaporated down under reduced pressure and the residue is subjected to fractional distilation to give 47 g (71% of theory) of a colorless oil of boiling point 100°-116° C./0.2 mm, consisting of about 30% of the cis isomer and 70% of the trans isomer (compound no. 64).

Workup

custom(about 3 hours)
filtrationThe discharged mixture is filtered under suction over kieselguhr
customthe filtrate is evaporated down under reduced pressure
customthe residue is subjected to fractional distilation
customto give 47 g (71% of theory) of a colorless oil of boiling point 100°-116° C./0.2 mm

Sources & evidence

ORD record: ord-dd6cad5c9c81435e8809df3bb5639a1c
Source dataset: uspto-grants-1990_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04897425

Linked notes

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