1-Methylpiperazine → HCID 57949407, compound

HRID 2427702Notes

Reaction equation

HRID 2427702 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:15][CH:14]=1)[CH2:5]2.[CH3:26][N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1.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.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[CH3:26][N:27]1[CH2:32][CH2:31][N:30]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[C:7](=[O:11])[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:15][CH:14]=2)[CH2:5]3)[CH2:29][CH2:28]1

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 57949704HCID 57949704, compound

Product 1

HCID 57949407HCID 57949407, compoundYield 41.1%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-bromo-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.039 g, 0.1 mmol), 1-methyl piperazine (0.022 mL, 0.2 mmol), Pd2.dba3 (0.009 g, 0.01 mmol), BINAP (0.012 g, 0.02 mmol), and sodium tertiary-butoxide (0.030 g, 0.3 mmol) in toluene (3 mL) was heated to reflux for 3 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-(4-Methyl-piperazin-1-yl)-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.017 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.37 (s, 3H), 2.58 (m, 4H), 3.32 (m, 4H), 4.20 (s, 2H), 4.72 (s, 2H), 6.83-7.36 (m, 11H), 7.75 (d, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h

Sources & evidence

ORD record
ord-e24adbdd074e4dc8bca7125e4487675a
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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