Cyclohexanone → HCID 24279299, compound

HRID 1011266Notes

Reaction equation

HRID 1011266 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:16]1(=O)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)Cl>[CH:16]1([N:13]2[CH2:14][CH2:15][N:10]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=3)[CH2:11][CH2:12]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

4

Reactant 2

HCID 7967CyclohexanoneHCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 24279299HCID 24279299, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the general procedure described above for the synthesis of 11-(4-nitrophenyl)-4-(pentan-3-yl)piperazine, treatment of 1-(4-nitrophenyl)piperazine (5.00 g, 24.1 mmol, 1.0 equiv.) with cyclohexanone (7.10 g, 72.4 mmol, 2.0 eq) in DCM (100 mL) at rt for 72 h provided the title compound as a yellow solid (4.80 g, 68% recovery, 89% purity as determined by LC/MS analysis @ UV 254 nm detection). In this case, an additional portion (25 mL) is added to the reaction mixture after 1 h. Upon addition of hexane (25 mL) to the crude residue, obtained from evaporation of the DCM extract, and stirring for 24 h the product precipitated from solution and was collected by filtration, washed with hexanes (2×25 mL), and dried under vacuum. The crude product is used in the next step without further purification. LCMS purity: 89% by UV 254 nm detection. LCMS-ESI (m/z): calcd for C16H23N3O2, 289; [M+H]+ found, 290.

Sources & evidence

ORD record
ord-dbbac192b1054d989de08e0c9fd69211
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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