Hydrochloric Acid → 1-(5-Bromopyrimidin-2-yl)-4-methylpiperidine-4-carboxylic acid

HRID 712236Notes

Reaction equation

HRID 712236 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][C:11]([CH3:19])([C:14]([O:16]CC)=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.Cl>O1CCOCC1.C(=O)([O-])O.[Na+]>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][C:11]([CH3:19])([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 66977024Ethyl 1-(5-bromopyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

Product 1

HCID 669772191-(5-Bromopyrimidin-2-yl)-4-methylpiperidine-4-carboxylic acidYield 73.7%

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

Ethyl 1-(5-bromopyrimidin-2-yl)-4-methylpiperidine-4-carboxylate (400 mg, 1.22 mmol) was stirred in dioxan (4 ml) and concentrated hydrochloric acid was added (2.8 ml). The reaction was stirred in a sealed tube at 100° C. for 5 h. LCMS indicated 90% conversion to the acid. The reaction was allowed to cool, diluted with a saturated aqueous solution of sodium hydrogen carbonate to adjust the pH to ˜5 at which point a solid precipitated. The solid was collected by filtration and dried to afford the desired product as a yellow solid (270 mg, 90% purity by LCMS) (77%).

Workup

  1. temperatureto cool
  2. customprecipitated
  3. filtrationThe solid was collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-85d5b38bce2c4b8abd139b4f4ebe1eb9
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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