Hydrochloric Acid → 1-(Pyrimidin-4-yl)piperidin-4-amine

HRID 451504Notes

Reaction equation

HRID 451504 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl>ClCCl.[OH-].[Na+]>[N:17]1[CH:18]=[CH:19][C:14]([N:11]2[CH2:10][CH2:9][CH:8]([NH2:7])[CH2:13][CH2:12]2)=[N:15][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 53426887tert-Butyl (1-(pyrimidin-4-yl)piperidin-4-yl)carbamate

Product 1

HCID 223943851-(Pyrimidin-4-yl)piperidin-4-amineYield 80%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution (1-pyrimidin-4-yl-piperidin-4-yl)-carbamic acid tert-butyl ester (1.00 g, 3.59 mmol) in dichloromethane (16 mL) was added HCl (2 M in diethylether, 8.98 mL, 18.0 mmol) and the reaction mixture was stirred at room temperature for 4 hours. The mixture was then diluted with NaOH (2 N) at 0° C. and extracted with dichloromethane. The combined organic extracts were then dried over sodium sulfate and filtered to afford the title compound (511 mg, 80%) as a light yellow solid.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe combined organic extracts were then dried over sodium sulfate
  3. filtrationfiltered

Sources & evidence

ORD record
ord-2202f1ed6f084b6f8a1f379a2e359e88
Source dataset
uspto-grants-2013_07
Patent number
US08486967B2

Reaction notes

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