1-Phenylpiperazine → HCID 67515135, compound

HRID 1400052Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[Na+].[C:27]1([N:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]3[CH:19]=[CH:18][C:17]([N:36]4[CH2:37][CH2:38][N:33]([C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH2:34][CH2:35]4)=[CH:16][CH:15]=3)([CH2:11]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

To a solution of 1-(4-bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane-3-carboxylic acid tert-butyl ester (2 g, 5.91 mmol) in anhydrous toluene (20 mL) were added Pd2(dba)3 (27 mg, 0.029 mmol), BINAP (36 mg, 0.059 mmol), sodium tert-butoxide (230 mg, 2.4 mmol) and 1-phenyl piperazine (1.05 g, 6.5 mmol) and reaction mixture was refluxed at 120° C. for 2 days. After the completion of reaction as confirmed by the TLC, excess solvent was evaporated under reduced pressure to afford crude compound which was purified by column chromatography (silica gel 0.8:9.2 EtOAc:Pet. ether) to afford pure title compound, (1.0 g, 2.38 mmol, 40%) as a thick gel.

Workup

customAfter the completion of reaction
customwas evaporated under reduced pressure
customto afford crude compound which
customwas purified by column chromatography (silica gel 0.8:9.2 EtOAc:Pet. ether)

Sources & evidence

ORD record: ord-5af8db0f8e6647f1bb04d37fe3c35c20
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906913B2

Reaction notes

Loading…