Methanol → 1-[4-Chloro-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acid

HRID 1678443Notes

Reaction equation

HRID 1678443 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([O:18]CC)=[O:17])[CH2:12][CH2:11]2)[N:3]=1.O.[OH-].[Li+].O.CO>O1CCCC1.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([OH:18])=[O:17])[CH2:12][CH2:11]2)[N:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 86644318Ethyl 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylate

Product 1

HCID 866443161-[4-Chloro-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylic acidYield 99.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 1-[4-chloro-6-(methylamino)-1,3,5-triazin-2-yl]-4-piperidinecarboxylate (983 mg, 3.28 mmol, 1.00 equiv) in tetrahydrofuran (21 ml) at 0° C., a premixed solution of lithium hydroxide monohydrate (275 mg, 6.56 mmol, 2.00 equiv) and water (7 ml) was added dropwise. Methanol (7 ml) was added. The reaction was allowed to warm to room temperature over 1 h and stirring was continued for 3 h. The solvent was removed under reduced pressure, yielding a colorless oil. Ethyl acetate was added to the oil, and the desired product precipitated as a white solid. The solid was filtered and dried under reduced pressure to provide 885 mg (99%) of the title compound. MS (ES+): m/e 272.0 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customyielding a colorless oil
  3. customthe desired product precipitated as a white solid
  4. filtrationThe solid was filtered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-6dd05f295fc84bc08c1b19b5d2f7ebfb
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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