Sodium Chloride → 1-[1-(4-Chloro-1,3,5-triazin-2-yl)piperidin-4-yl]piperidin-3-ol

HRID 2175087Notes

Reaction equation

HRID 2175087 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[N:16]1([CH:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:21][CH2:20][CH2:19][CH:18]([OH:22])[CH2:17]1.[Na+].[Cl-]>C(#N)C>[Cl:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([N:26]2[CH2:25][CH2:24][CH:23]([N:16]3[CH2:21][CH2:20][CH2:19][CH:18]([OH:22])[CH2:17]3)[CH2:28][CH2:27]2)[N:7]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 178102,4-Dichloro-1,3,5-triazineHCID 21091574[1,4'-Bipiperidin]-3-ol

Product 1

HCID 532524851-[1-(4-Chloro-1,3,5-triazin-2-yl)piperidin-4-yl]piperidin-3-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

200 mg (1.27 mmol) of 2,4-dichloro-1,3,5-triazine are dissolved in 2 ml of acetonitrile, cooled to 0° C., 176 μl of triethylamine and 223 mg (1.27 mmol) of 1,4′-bipiperidinyl-3-ol are added. The reaction mixture is stirred at 0° C. for 2 h and subsequently at room temperature for 48 h. Sat. NaCl solution is subsequently added, and the mixture is extracted three times with ethyl acetate. The combined organic phases are washed with 1N NaOH and water, dried over Na2SO4 and evaporated.

Workup

  1. extractionthe mixture is extracted three times with ethyl acetate
  2. washThe combined organic phases are washed with 1N NaOH and water
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-92c8111903d646b9a13d0796c01b5651
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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