Water → HCID 22557720, compound

HRID 1615392Notes

Reaction equation

HRID 1615392 reaction equation
[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10](F)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[NH2:21][CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.O>CS(C)=O>[C:1]([O:5][C:6](=[O:14])[C:7]1[CH:12]=[CH:11][C:10]([N:25]2[CH2:26][CH2:27][CH:22]([NH2:21])[CH2:23][CH2:24]2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4243614-PiperidinamineHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 22557720HCID 22557720, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
120 °C

Procedure

4-fluorobenzoic acid tert-butyl ester (19.6 g, 100 mmol) was dissolved in dimethyl sulfoxide (hereinafter referred to as DMSO) (50 ml), and potassium carbonate (20.7 g, 150 mmol) and 4-aminopiperidine (11.0 g, 110 mmol) were added thereto, followed by stirring at 120° C. for 17 hours. After the reaction mixture was cooled to room temperature, water was added to the mixture, and the precipitate was collected by filtration, thereby obtaining 4-(4-aminopiperidin-1-yl)-benzoic acid tert-butyl ester (23.3 g, 84%) as a milky-white solid.

Workup

  1. additionwere added
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-cd7894c7a6794d0d835866f26849e634
Source dataset
uspto-grants-2014_07
Patent number
US08765750B2

Reaction notes

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