Dimethylformamide → 4-Nitro-3-{[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amino}benzonitrile

HRID 2064086Notes

Reaction equation

HRID 2064086 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:5](F)[CH:4]=1)#[N:2].Cl.Cl.[O:15]1[CH2:20][CH2:19][CH:18]([N:21]2[CH2:26][CH2:25][CH:24]([NH2:27])[CH2:23][CH2:22]2)[CH2:17][CH2:16]1.C(N(C(C)C)CC)(C)C.CN(C)C=O>O>[N+:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][C:5]=1[NH:27][CH:24]1[CH2:23][CH2:22][N:21]([CH:18]2[CH2:19][CH2:20][O:15][CH2:16][CH2:17]2)[CH2:26][CH2:25]1)([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27833993-Fluoro-4-nitrobenzonitrileHCID 451567511-(Oxan-4-yl)piperidin-4-amine dihydrochloride

Product 1

HCID 691225114-Nitro-3-{[1-(tetrahydro-2H-pyran-4-yl)-4-piperidinyl]amino}benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
200 °C

Procedure

4-Cyano-2-fluoro-1-nitrobenzene (300 mg, 0.0018 mol, 1 eq), 1-(tetrahydro-2H-pyran-4-yl)-4-piperidinamine (D9, 330 mg, 0.0018 mol, 1 eq), diisopropylethylamine (350 mg, 0.0027 mol, 1.5 eq), and dimethylformamide (5 ml) were combined, heated to 200° C. and held for 1 min in a microwave reactor. 100 ml of water was then added and the reaction extracted with 2×75 ml dichloromethane. The dichloromethane layers were combined, dried with sodium sulfate, and evaporated to yield the title compound which was used without further purification in the next step. MS (ESI): 331 [M+H]+.

Workup

  1. extractionthe reaction extracted with 2×75 ml dichloromethane
  2. dry with materialdried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-1b11be07597e44d2a48ce293b747af96
Source dataset
uspto-grants-2012_10
Patent number
US08288413B2

Reaction notes

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