4-Piperidinecarboxylic acid → HCID 67338015, compound

HRID 1678439Notes

Reaction equation

HRID 1678439 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][CH3:15])[N:3]=1.[NH:16]1[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]1.[OH-].[Na+]>CC#N.O>[CH3:15][NH:14][C:4]1[N:5]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=[C:2]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]2)[N:3]=1

Participants

6

Reactant 3

HCID 37734-Piperidinecarboxylic acidHCID 14798Sodium HydroxideHCID 16082HCID 16082, compound

Product 1

HCID 67338015HCID 67338015, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-N-methyl-6-phenyl-1,3,5-triazin-2-amine (10.0 g, 45.3 mmol, 1.00 equiv) dissolved in 1:1 CH3CN:H2O (60 mL) was cooled (0° C.), and 4-piperidinecarboxylic acid (11.7 g, 90.6 mmol, 2.00 equiv) was added. The pH of the reaction mixture was adjusted to 9-10 by treating with 1 N NaOH. The pH was maintained at 9-10 for 24 hours (product formation monitored by LCMS). The mixture was diluted with water, and filtered to provide the crude product (filtered solid was washed with additional water). The resulting solid was purified by HPLC to afford 9.1 g of the title compound. MS (ES+): m/e 314.2 [M+H]+.

Workup

  1. additionwas added
  2. temperatureThe pH was maintained at 9-10 for 24 hours (product formation monitored by LCMS)
  3. filtrationfiltered
  4. customto provide the crude product (filtered solid was washed with additional water)
  5. customThe resulting solid was purified by HPLC

Sources & evidence

ORD record
ord-2678dab42db842b192cdb09d08c3b120
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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