Triethylamine → HCID 80652557, compound

HRID 1755344Notes

Reaction equation

HRID 1755344 reaction equation
F[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.Cl.[CH3:10][C:11]1([CH3:16])[CH2:15][CH2:14][NH:13][CH2:12]1.CCN(CC)CC>O>[CH3:10][C:11]1([CH3:16])[CH2:15][CH2:14][N:13]([C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=2)[CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27613996-Fluoropyridin-2-amineHCID 467360573,3-Dimethylpyrrolidine--hydrogen chloride (1/1)

Product 1

HCID 80652557HCID 80652557, compoundYield 78.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
205 °C

Procedure

A mixture of 6-fluoropyridin-2-amine (0.5 g, 4.46 mmol), 3,3-dimethylpyrrolidine hydrochloride (0.73 g, 5.35 mmol) and Et3N (1.08 g, 10.7 mmol) in water (0.2 mL) was heated to 205° C. for 0.5 h in a sealed tube in a microwave oven then concentrated in vacuo. The residue was purified by chromatography (silica gel, 10 g, 200-300 mesh, ethyl acetate:petroleum ether=1:15) to afford 6-(3,3-dimethylpyrrolidin-1-yl)pyridin-2-amine (0.67 g, 78%) as a yellow oil. LC-MS: [M+1]+=192, tR=1.187 min.

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was purified by chromatography (silica gel, 10 g, 200-300 mesh, ethyl acetate:petroleum ether=1:15)

Sources & evidence

ORD record
ord-37420b0b6f084294a47767a1c9ad613e
Source dataset
uspto-grants-2015_10
Patent number
US09169259B2

Reaction notes

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