N-[2-(1-pyrrolidinylmethyl)-6-quinolinyl]acetamide → 2-(1-Pyrrolidinylmethyl)-6-quinolinylamine

HRID 585305Notes

Reaction equation

[N:1]1([CH2:6][C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH:17]C(=O)C)[CH:13]=3)[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>Cl>[N:1]1([CH2:6][C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][CH:11]=[C:12]([NH2:17])[CH:13]=3)[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 110 °C

Procedure

To the N-[2-(1-pyrrolidinylmethyl)-6-quinolinyl]acetamide (5.53 g, 20.5 mmol) obtained in 1) of Example 7 was added concentrated hydrochloric acid (100 ml), the mixture was stirred at 110° C. for 1 hour, and the solvent was distilled off under reduced pressure. To the resulting residue was added ethyl acetate, the mixture was washed with an aqueous potassium carbonate solution and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain the titled compound (4.56 g) as a powder from ethyl acetate-hexane.

Workup

distillationthe solvent was distilled off under reduced pressure
additionTo the resulting residue was added ethyl acetate
washthe mixture was washed with an aqueous potassium carbonate solution
dry with materialan aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-e9e2182d72664dcc9b3a40e108dcb3f6
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06930185B2

Reaction notes

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