Potassium Carbonate → HCID 66664684, compound

HRID 1773583Notes

Reaction equation

Cl[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[N:9]2)=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C(=O)([O-])[O-].[K+].[K+].[C:21]([O:25][C:26](=[O:35])[NH:27][CH2:28][CH:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1)([CH3:24])([CH3:23])[CH3:22]>CN(C)C=O>[C:21]([O:25][C:26](=[O:35])[NH:27][CH2:28][CH:29]1[CH2:30][CH2:31][N:32]([C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][CH:8]=[N:9]3)=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])[CH2:33][CH2:34]1)([CH3:24])([CH3:22])[CH3:23]

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 7-chloro-6-nitro-quinoline (974 mg, 4.67 mmol) in N,N-dimethylformamide (25 mL) were added potassium carbonate (1.93 g, 14.01 mmol) and piperidin-4-ylmethyl-carbamic acid tert-butyl ester (1.00 g, 4.67 mmol) and the resulting mixture was heated at 100° C. overnight. The reaction mixture was cooled and partitioned between water (500 mL) and ethyl acetate (300 mL). The organic layer was separated, washed twice with water (500 mL), dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified twice by flash chromatography to afford 415 mg of [1-(6-nitro-quinolin-7-yl)-piperidin-4-ylmethyl]-carbamic acid tert-butyl ester as an orange solid.

Workup

temperatureThe reaction mixture was cooled
custompartitioned between water (500 mL) and ethyl acetate (300 mL)
customThe organic layer was separated
washwashed twice with water (500 mL)
dry with materialdried over anhydrous sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe crude residue was purified twice by flash chromatography

Sources & evidence

ORD record: ord-bf181770a36b456ea198d81616074d1c
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09255110B2

Reaction notes

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