Hydrochloric Acid → HCID 58576452, compound

HRID 511100Notes

Reaction equation

HRID 511100 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O.ClCCl.C(OC(=O)C)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][N:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 923422-Chloro-5-(trifluoromethyl)pyridineHCID 12682914-Amino-1-Boc-piperidine

Product 1

HCID 58576452HCID 58576452, compoundYield 55%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A solution of 4-amino-piperidine-1-carboxylic acid tert-butyl ester (400 mg; 2.0 mmol), 2-chloro-5-trifluoromethyl-pyridine (362 mg; 2.0 mmol) and potassium carbonate (280 mg; 2.0 mmol) in dimethylsulfoxide (3 mL) is heated 10 hours at 120° C. The reaction is then cooled to room temperature, water (20 mL) is added and the pH is set to 4-5 by addition of aq. 1N hydrochloric acid. The aqueous layer is then extracted with dichloromethane (4×20 mL), the combined organic layers are dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue obtained is finally purified by column chromatography on silica gel (dichloromethane and then dichloromethane:ethylacetate 8:1) to afford the desired product (380 mg; 1.10 mmol).

Workup

  1. extractionThe aqueous layer is then extracted with dichloromethane (4×20 mL)
  2. dry with materialthe combined organic layers are dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis finally purified by column chromatography on silica gel (dichloromethane

Sources & evidence

ORD record
ord-7b3ce21819e34585acb31acd34a13938
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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