Potassium Carbonate → HCID 86636687, compound

HRID 388779Notes

Reaction equation

HRID 388779 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][CH2:23][N:24](C(C)C)C(C)C.BrCC#N>CC#N>[C:23]([CH2:22][N:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:3][CH2:2]1)#[N:24]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 86636687HCID 86636687, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl piperidin-4-ylmethylcarbamate (5 g, 23.2 mmol) was dissolved in CH3CN (40 mL). Potassium carbonate (3.5 g, 25 mmol), DIPEA (4.4 mL, 25 mmol) and bromoacetonitrile (2.77 g, 23.2 mmol) were added, and the mixture was stirred at room temperature overnight. The solution was then concentrated and saturated NaHCO3 (40 mL) was added. The mixture was extracted with CH2Cl2 (4×30 mL). The extract was dried over anhydrous Na2SO4. The dried extract was passed through a silica gel plug, and the desired compound was eluted off with EtOAc. The product was further purified by crystallization from EtOAc/petroleum ether as a white solid (5.4 g, 92%).

Workup

  1. concentrationThe solution was then concentrated
  2. additionsaturated NaHCO3 (40 mL) was added
  3. extractionThe mixture was extracted with CH2Cl2 (4×30 mL)
  4. dry with materialThe extract was dried over anhydrous Na2SO4
  5. extractionThe dried extract
  6. washthe desired compound was eluted off with EtOAc
  7. customThe product was further purified by crystallization from EtOAc/petroleum ether as a white solid (5.4 g, 92%)

Sources & evidence

ORD record
ord-5a0868fa9cb9496f89306c17f74c799c
Source dataset
uspto-grants-2013_02
Patent number
US08377968B2

Reaction notes

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