Cyclobutanone → HCID 57664371, compound

HRID 1011265Notes

Reaction equation

HRID 1011265 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH2:19][CH3:20])[CH2:17]C)[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+](C1C=CC(N2CCNCC2)=CC=1)([O-])=O.C1(=O)CCC1>C(Cl)Cl>[CH:16]1([N:13]2[CH2:12][CH2:11][N:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:15][CH2:14]2)[CH2:17][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 14496CyclobutanoneHCID 804471-(4-Nitrophenyl)piperazineHCID 20735178HCID 20735178, compound

Product 1

HCID 57664371HCID 57664371, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the general procedure described above for the synthesis of 1-(4-nitrophenyl)-4-(pentan-3-yl)piperazine, treatment of 1-(4-nitrophenyl)piperazine (5.00 g, 24.1 mmol, 1.0 equiv.) with cyclobutanone (3.38 g, 48.3 mmol, 2 equiv.) in DCM (100 mL) at RT for 72 h provided the title compound as a yellow solid (4.96 g, 99% recovery, 87% purity as determined by LC/MS analysis @ UV 254 nm detection). In this case, 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, is collected by filtration, washed with hexanes (2×25 ml), and was dried under vacuum. The crude product is used in the next step without further purification. LCMS-ESI (m/z): calcd for C14H19N3O2, 261; [M+H]+ found, 262.

Sources & evidence

ORD record
ord-9e531c50a45b485ea4ccb9d71981f4b8
Source dataset
uspto-grants-2011_07
Patent number
US07977352B2

Reaction notes

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