Triethylamine → 4-(1-Cyclobutyl piperidin-4-yloxy)benzonitrile

HRID 268719Notes

Reaction equation

HRID 268719 reaction equation
FC(F)(F)C(O)=O.[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1.C(N(CC)CC)C.[C:30]1(=O)[CH2:33][CH2:32][CH2:31]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:30]1([N:8]2[CH2:9][CH2:10][CH:11]([O:14][C:15]3[CH:22]=[CH:21][C:18]([C:19]#[N:20])=[CH:17][CH:16]=3)[CH2:12][CH2:13]2)[CH2:33][CH2:32][CH2:31]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14496CyclobutanoneHCID 5049666Sodium triacetoxyborohydrideHCID 179863194-(4-Piperidinyloxy)benzonitrile trifluoroacetate

Product 1

HCID 98137774-(1-Cyclobutyl piperidin-4-yloxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Piperidinyloxy)benzonitrile trifluoroacetate (D22) (2.2 g) was dissolved in DCM (50 ml) and triethylamine (1.92 ml) was added followed by cyclobutanone (0.64 g). The mixture was stirred for 5 min, then sodium triacetoxyborohydride (1.94 g) was added and the reaction was stirred at rt under argon overnight. The reaction mixture was then washed with saturated potassium carbonate solution (3×30 ml) and brine (30 ml). The organic layer was dried (MgSO4) and evaporated to give the title compound (D23) as a white solid (1.91 g). 1H NMR δ (CDCl3): 7.56 (2H, d, J=6.84 Hz), 6.93 (2H, d, J=6.80 Hz), 4.41 (1H, m), 2.77 (1H, m), 2.75 (2H, m), 2.30 (2H, m), 2.06 (4H, m), 1.87 (4H, m), 1.66 (2H, m).

Workup

  1. stirringthe reaction was stirred at rt under argon overnight
  2. washThe reaction mixture was then washed with saturated potassium carbonate solution (3×30 ml) and brine (30 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-1f68a7305cef4cfa92d31f331cd5747a
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

Loading…