5,6,7,8-Tetrahydro-2-naphthylamine → (5,6,7,8-Tetrahydro-naphthalen-2-yl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine

HRID 1094343Notes

Reaction equation

[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[NH2:11].[F:12][C:13]([F:24])([F:23])[C:14]1[N:19]=[CH:18][C:17]([CH2:20][C:21]#N)=[CH:16][CH:15]=1>CO.[Pd]>[CH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][C:2]=1[NH:11][CH2:21][CH2:20][C:17]1[CH:18]=[N:19][C:14]([C:13]([F:24])([F:12])[F:23])=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 5,6,7,8-tetrahydro-naphthalen-2-ylamine (1.132 g, 6.08 mmol, commercially available) and (6-trifluoromethyl-pyridin-3-yl)-acetonitrile (distilled 166-175° C./2 mb, 0.985 g, 6.69 mmol, prepared as per example 1, step 1) in MeOH (10 mL) was treated with HCO2NH4 (2.301 g, 36.5 mmol) and 10% Pd/C (250 mg) and stirred at 80° C. for 1.5 h. Filtration, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40) afforded the title compound (1.333 g, 68%) as an off-white solid. MS m/e: 321.1 [M+H]+.

Workup

filtrationFiltration, concentration and purification by chromatography (SiO2, heptane:ethyl acetate=95:5 to 60:40)

Sources & evidence

ORD record: ord-26c516f9aee442f89d739312d88b16e4
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133909B2

Reaction notes

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