Sodium Iodide → 4-[3-(3-tert-Butoxycarbonylamino-piperidin-1-yl)-propyl]-benzoic acid methyl ester

HRID 509901Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12]OS(C)(=O)=O)=[CH:6][CH:5]=1.[C:19]([O:23][C:24](=[O:32])[NH:25][CH:26]1[CH2:31][CH2:30][CH2:29][NH:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:28]2[CH2:29][CH2:30][CH2:31][CH:26]([NH:25][C:24]([O:23][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:32])[CH2:27]2)=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 90 °C

Procedure

4-(3-Methanesulfonyloxy-propyl)-benzoic acid methyl ester (800 mg, 2.9 mmol), piperidin-3-yl-carbamic acid tert-butyl ester (290 mg, 1.45 mmol), potassium carbonate (500 mg, 3.6 mmol) and sodium iodide (100 mg 0.67 mmol) in acetonitrile (20 ml) are heated under reflux for two days and evaporated. The residue is taken up in dimethylsulfoxide (10 ml) and stirred at 90° C. for 5 h. The resulting mixture is purified by preparative HPLC-MS (MeOH/H2O+0.1% TFA). Potassiumcarbonate solution is added to the product, extracted with ethyl acetate, the organic phase is dried over Na2SO4 and concentrated in vacuo. LC (method F): tR=1.66 min; Mass spectrum (ESI+): m/z=377 [M+H]+.

Workup

temperatureunder reflux for two days
customevaporated
customThe resulting mixture is purified by preparative HPLC-MS (MeOH/H2O+0.1% TFA)
additionPotassiumcarbonate solution is added to the product
extractionextracted with ethyl acetate
dry with materialthe organic phase is dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-28fb81251ba64e829d4d39ded25d464c
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096548B2

Reaction notes

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