Sodium hydride → HCID 178511712, compound

HRID 22943

Reaction equation

HRID 22943 reaction equation
[H-].[Na+].Cl.[NH2:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([OH:11])[CH2:7][CH2:6]1.Cl[C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1>O1CCCC1>[N:14]1[CH:15]=[CH:16][CH:17]=[N:18][C:13]=1[O:11][C@H:8]1[CH2:9][CH2:10][C@H:5]([NH2:4])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 178479278HCID 178479278, compound

Product 1

HCID 178511712HCID 178511712, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60% sodium hydride was added to 10 ml of a tetrahydrofuran suspension containing 1.00 g of trans-4-aminocyclohexanol hydrochloride and the mixture was refluxed for 1 hour. After cooling to room temperature, 2-chloropyrimidine was slowly added thereto and the mixture was stirred at room temperature for 6 hours. The reaction mixture was poured into ice-cold water and extracted with chloroform. The extract was washed with brine and dried over anhydrous sodium sulfate, and then, the solvent was removed under reduced pressure. The residue was purified by NH-silica gel column chromatography (solvent: ethyl acetate-hexane (1:4) to chloroform alone) to obtain 788 mg of trans-4-(2-pyrimidinyloxy)cyclohexylamine (Reference Example 9-46 in Table 6).

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. additionThe reaction mixture was poured into ice-cold water
  3. extractionextracted with chloroform
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by NH-silica gel column chromatography (solvent

Sources & evidence

ORD record
ord-177949fd58514cb08143173f2492b15a
Source dataset
uspto-grants-2005_02
Patent number
US06849622B2

Linked notes

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