Acetic Acid → N-cyclopropyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidin-4-amine

HRID 1409688Notes

Reaction equation

HRID 1409688 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([N:12]3[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCl>[CH:19]1([NH:22][CH:15]2[CH2:16][CH2:17][N:12]([C:10]3[O:9][N:8]=[C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[N:11]=3)[CH2:13][CH2:14]2)[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5049666Sodium triacetoxyborohydrideHCID 682902121-(3-Phenyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-one

Product 1

HCID 68289604N-cyclopropyl-1-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidin-4-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1-(3-phenyl-[1,2,4]oxadiazol-5-yl)-piperidin-4-one (400 mg), cyclopropylamine (120 μL), sodium triacetoxyborohydride (420 mg), and glacial acetic acid (0.20 mL) in dichloromethane (7 mL) is stirred for two days at room temperature. Dichloromethane is added and the mixture is washed with aqueous K2CO3 solution. The organic phase is dried over Na2SO4 and concentrated in vacuo to afford the title compound. TLC: rf=0.30 (silica gel, CH2Cl2/MeOH 95:5); Mass spectrum (ESI+): m/z=285 [M+H]+.

Workup

  1. washthe mixture is washed with aqueous K2CO3 solution
  2. dry with materialThe organic phase is dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0018413305a94f138368da39b32c1dc4
Source dataset
uspto-grants-2014_12
Patent number
US08921398B2

Reaction notes

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