Acetone → HCID 17986269, compound

HRID 268725Notes

Reaction equation

HRID 268725 reaction equation
Cl.[Cl:2][C:3]1[CH:10]=[C:9]([O:11][CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].C(N(CC)CC)C.[CH3:25][C:26]([CH3:28])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:2][C:3]1[CH:10]=[C:9]([O:11][CH:12]2[CH2:17][CH2:16][N:15]([CH:26]([CH3:28])[CH3:25])[CH2:14][CH2:13]2)[CH:8]=[CH:7][C:4]=1[C:5]#[N:6]

Participants

6

Reactant 4

HCID 180AcetoneHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 179862902-Chloro-4-(piperidin-4-yloxy)-benzonitrile hydrochloride

Product 1

HCID 17986269HCID 17986269, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Chloro-4-(4-piperidinyloxy)benzonitrile hydrochloride (D30) (1.5 g) was dissolved in DCM (40 ml) and triethylamine (2.29 ml) was added followed by acetone (0.64 g). The mixture was stirred for 5 min and then sodium triacetoxyborohydride (1.94 g) was added and the reaction stirred at rt under argon overnight. The reaction mixture was then washed with saturated potassium carbonate solution (2×40 ml) and brine (40 ml). The organic layer was dried (MgSO4) and evaporated to give the title compound (D31) as a white solid (1.51 g). MS electrospray (+ion) 279 (MH+).

Workup

  1. stirringthe reaction stirred at rt under argon overnight
  2. washThe reaction mixture was then washed with saturated potassium carbonate solution (2×40 ml) and brine (40 ml)
  3. dry with materialThe organic layer was dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-3c53d664443045b28a4e9dbedddb7741
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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