Ethanol → 4-amino-4-methyl-N-(2-pyrimidinyl)piperidine

HRID 1445351Notes

Reaction equation

HRID 1445351 reaction equation
C(O)C.[NH2:4][C:5]1([CH3:11])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Cl[C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:4][C:5]1([CH3:11])[CH2:10][CH2:9][N:8]([C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:7][CH2:6]1

Participants

6

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 210904454-Methylpiperidin-4-amine

Product 1

HCID 218825664-amino-4-methyl-N-(2-pyrimidinyl)piperidineYield 65.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2 ml of an ethanol suspension containing 260 mg of 4-amino-4-methylpiperidine (synthesized according to a method described in U.S. Pat. No. 5,821,240), 237 mg of 2-chloropyrimidine and 858 mg of potassium carbonate was stirred at 50° C. for 12 hours. The reaction mixture was poured into water, and extracted with chloroform. The extract was washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The residue was purified by silica gel flash column chromatography [solvent: chloroform-methanol-aqueous ammonia (300′:10:1)] to obtain 259 mg of 4-amino-4-methyl-N-(2-pyrimidinyl)piperidine (Reference Example 8-1 in Table 9).

Workup

  1. customsynthesized
  2. extractionextracted with chloroform
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel flash column chromatography [solvent

Sources & evidence

ORD record
ord-d7f8b4a72a26430a99b45e94d606649d
Source dataset
uspto-grants-2010_02
Patent number
US07666869B2

Reaction notes

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