Piperonylamine → 8-methyl-5-(2-(6-(trifluoromethyl)pyridin-3-yl)ethyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1773250Notes

Reaction equation

[C:1]1([CH3:21])[CH:6]=[CH:5][C:4]([N:7]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:19])[F:18])=[N:15][CH:16]=2)N)=[CH:3][CH:2]=1.Cl.O.[NH:24]1[CH2:29][CH2:28][C:27](=O)[CH2:26][CH2:25]1>O1CCOCC1.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>[CH3:21][C:1]1[CH:6]=[CH:5][C:4]2[N:7]([CH2:9][CH2:10][C:11]3[CH:16]=[N:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=3)[C:27]3[CH2:28][CH2:29][NH:24][CH2:25][C:26]=3[C:3]=2[CH:2]=1

Participants

Conditions

Temperature: 100 °C

Procedure

5-(2-(1-p-Tolylhydrazinyl)ethyl)-2-(trifluoromethyl)pyridine (88 mg, 0.29 mmol) was dissolved in 1,4-dioxane (2 mL) and 4-piperidone hydrate hydrochloride was added with one drop of TFA. The reaction mixture became acidic. The mixture was heated at 100° C. for 2 h. The reaction was monitored by TLC and LCMS. After completion of reaction, the mixture was diluted with sat. NaHCO3 solution and extracted with EtOAc. The organic extracts were dried over anhydrous sodium sulfate and concentrated. The compound was purified by reverse phase chromatography. 1HNMR (CD3OD, TFA salt) d (ppm): 8.20 (s, 1H), 7.60 (m, 2H), 7.25 (d, 1H), 7.18 (d, 1H), 6.98 (d, 1H), 4.40 (m, 4H), 3.50 (t, 2H), 3.20 (m, 2H), 2.82 (t, 2H), 2.40 (s, 3H).

Workup

customAfter completion of reaction
extractionextracted with EtOAc
dry with materialThe organic extracts were dried over anhydrous sodium sulfate
concentrationconcentrated
customThe compound was purified by reverse phase chromatography

Sources & evidence

ORD record: ord-7b2280d4ac3642bb92b9cec848984728
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255094B2

Reaction notes

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