N-Piperidinoethanol → HCID 23362071, compound

HRID 1082087Notes

Reaction equation

HRID 1082087 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:16])[N:3]=1.[N:17]1([CH2:23][CH2:24][OH:25])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.[H-].[Na+].[ClH:28].C(O)C>O1CCCC1.C(O)C>[ClH:1].[ClH:28].[CH3:15][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[CH:7]=[C:2]([O:25][CH2:24][CH2:23][N:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[N:3]=[C:4]([CH3:16])[N:5]=2)=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 18232N-PiperidinoethanolHCID 24758Sodium hydrideHCID 21887872Ethanol hydrochlorideHCID 233620664-Chloro-6-(4-methoxyphenyl)-2-methylpyrimidine

Product 1

HCID 23362071HCID 23362071, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.17 g of 4-chloro-6-(4-methoxyphenyl)-2-methylpyrimidine and 0.65 g of 2-piperidinoethanol were dissolved in 10 ml of dried tetrahydrofuran. After the addition of 60% sodium hydride 0.2 g, the mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into ice-water, and then was extracted with ethyl acetate. The extract was washed with water and was dried with anhydrous magnesium sulfate, and then this was evaporated in vacuo. The residue was purified with column chromatography with silica gel(Wako gel c-200 150 g, elution with chloroform and then chloroform: methanol=99:1), resulting 1.3 g of oily substance. This was dissolved in 10 ml of ethanol, 3 ml of 20% ethanol hydrochloride was added and evaporated in vacuo. Ether was added to the residue to crystallize. Whereby 1.32 g of crystals were obtained. These were recrystallized with isopropanol, resulting to obtain 0.83 g of crystals. Melting point is 165° to 167° C.

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialwas dried with anhydrous magnesium sulfate
  4. customthis was evaporated in vacuo
  5. customThe residue was purified with column chromatography with silica gel(
  6. washWako gel c-200 150 g, elution with chloroform
  7. customchloroform: methanol=99:1), resulting 1.3 g of oily substance
  8. customevaporated in vacuo
  9. additionEther was added to the residue
  10. customto crystallize

Sources & evidence

ORD record
ord-5bd9bc729fee4bd6b73622d63f8e31a5
Source dataset
uspto-grants-1996_12
Patent number
US05589477

Reaction notes

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