1-Pyrrolidineethanamine → N-(2-(pyrrolidin-1-yl)ethyl)-3-(trifluoromethyl)pyridin-2-amine

HRID 2079691Notes

Reaction equation

F[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:12][CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN1C(=O)CCC1>[N:15]1([CH2:14][CH2:13][NH:12][C:2]2[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 85 °C

Procedure

To the solution of 2-fluoro-3-(trifluoromethyl)pyridine (990 mg, 6 mmole) in 5 ml of NMP, 2-aminoethylpyrrolidine (1.13 ml, 9 mmole) and triethylamine (1 ml, 7.2 mmole) were added. The reaction solution was stirred at 85° C. for overnight. The reaction mixture was poured into 40 ml of saturated NaHCO3 and extracted with ethyl acetate (2×80 ml). The combined organic layers were washed with water (2×30 ml) and brine (30 ml), then dried over Na2SO4 and evaporated in vacuo to give a brown oily N-(2-(pyrrolidin-1-yl)ethyl)-3-(trifluoromethyl)pyridin-2-amine (1.61 g). ES/MS m/z 260.1 (MH+).

Workup

extractionextracted with ethyl acetate (2×80 ml)
washThe combined organic layers were washed with water (2×30 ml) and brine (30 ml)
dry with materialdried over Na2SO4
customevaporated in vacuo

Sources & evidence

ORD record: ord-49e755b97b824b5fa8e6af1c541e34b0
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07932262B2

Reaction notes

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