1-Methylpiperazine → HCID 57949744, compound

HRID 2427700Notes

Reaction equation

HRID 2427700 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][N:7]([CH2:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[CH:16][CH:15]=3)[C:8]2=[O:11])=[CH:4][CH:3]=1.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]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>[CH3:27][N:28]1[CH2:33][CH2:32][N:31]([C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][N:7]([CH2:12][CH2:13][C:14]4[CH:19]=[CH:18][C:17]([O:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)=[CH:16][CH:15]=4)[C:8]3=[O:11])=[CH:4][CH:3]=2)[CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 67251495HCID 67251495, compound

Product 1

HCID 57949744HCID 57949744, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6-Bromo-2-[2-(4-phenoxy-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (0.134 g, 0.33 mmol), 1-methyl piperazine (0.048 mL, 0.43 mmol), Pd2.dba3 (0.009 g, 0.01 mmol), BINAP (0.012 g, 0.02 mmol), and sodium tertiary-butoxide (0.048 g, 0.5 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 6-(4-Methyl-piperazin-1-yl)-2-[2-(4-phenoxy-phenyl)-ethyl]-2,3-dihydro-isoindol-1-one (0.03 g, 41%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.36 (s, 3H), 2.57 (m, 4H), 2.93 (t, 2H), 3.32 (m, 4H), 3.81 (t, 2H), 4.16 (s, 2H), 6.82-7.35 (m, 11H), 7.68 (d, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h

Sources & evidence

ORD record
ord-a499a90a99dc486bab24e5f1027b9737
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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