5-Nitro-2-indanone → 1-(5-Nitro-2,3-dihydro-1H-inden-2-yl)-4-[2-(4-nitrophenyl)ethyl]piperazine

HRID 1519592Notes

Reaction equation

HRID 1519592 reaction equation
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:7][CH:6]=1)([O-:4])=[O:3].[N+:19]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][C:26](=O)[CH2:25]2)([O-:21])=[O:20].C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[N+:19]([C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[CH2:27][CH:26]([N:16]1[CH2:17][CH2:18][N:13]([CH2:12][CH2:11][C:8]3[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=3)[CH2:14][CH2:15]1)[CH2:25]2)([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 15020665-Nitro-2-indanoneHCID 5003444Sodium cyanoborohydrideHCID 666440061-[2-(4-Nitrophenyl)ethyl]piperazine hydrochloride

Product 1

HCID 866944771-(5-Nitro-2,3-dihydro-1H-inden-2-yl)-4-[2-(4-nitrophenyl)ethyl]piperazine

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

A mixture of 1-[2-(4-Nitrophenyl)ethyl]piperazine hydrochloride (50 mg, 0.18 mmol), 5-nitro-1,3-dihydro-2H-inden-2-one (39 mg, 0.22 mmol), sodium cyanoborohydride (58 mg, 0.92 mmol, and Titanium (IV) Isopropoxide (0.54 mL, 1.8 mmol) was allowed to stir at RT for 3 hours. LC showed formation of the desired product. The reaction was diluted with EtOAc, washed with brine, dried over sodium sulfate, filtered, concentrated and purified by mass-directed HPLC (0.1% TFA in water and acetonitrile). LC-MS (IE, m/z): 397 (M+1)+. (0.31 μM)

Sources & evidence

ORD record
ord-7def72c6f4e6416e8be99ac08a76d5e7
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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