Water → HCID 21959661, compound

HRID 2239347Notes

Reaction equation

HRID 2239347 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].Cl[C:12]1[CH:17]=[C:16]([C:18]#[N:19])[CH:15]=[CH:14][N:13]=1.O>CS(C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][C:12]2[CH:17]=[C:16]([CH:15]=[CH:14][N:13]=2)[C:18]#[N:19])[CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 660484-Piperidinol, 1-methyl-HCID 5686382-Chloro-4-cyanopyridine

Product 1

HCID 21959661HCID 21959661, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
60 °C

Procedure

1-Methylpiperidin-4-ol (0.457 g, 3.97 mmol) was dissolved in 5 mL of DMSO under argon and NaH (0.173 g, 3.97 mmol) was added. The reaction mixture was stirred at ambient temperature for 3 h and 30 min at 60° C. The mixture was allowed to cool and 2-chloro-4 pyridinecarbonitrile (0.500 g, 3.97 mmol) was added. The mixture was stirred for 2 h at ambient temperature and subsequently poured into 100 mL of water, extracted three times with EtOAc. The combined organic layer washed with water, dried over Na2SO4 and evaporated. The crude product was purified by preparative HPLC (Kromasil C8 50×250 mm, CH3CN/0, 2% HOAc 5/95-50/50). The product was freeze dried from water. Yield: 0.250 g (32%). 1H NMR (500 MHz, CD3OD) δ8.32 (d, 1H), 7.19 (dd, 1H), 7.12 (bs, 1H), 5.14 (m, 1H), 2.75 (m, 2H), 2.38 (m, 2H), 2.32 (s, 3H), 2.06 (m, 2H), 1.84 (m, 2H).

Workup

  1. temperatureto cool
  2. stirringThe mixture was stirred for 2 h at ambient temperature
  3. extractionextracted three times with EtOAc
  4. washThe combined organic layer washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customThe crude product was purified by preparative HPLC (Kromasil C8 50×250 mm, CH3CN/0, 2% HOAc 5/95-50/50)
  8. dry with materialdried from water

Sources & evidence

ORD record
ord-95fd01c630654447b04d096249096e3c
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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