HCID 57419565, compound → 1-[4-(4-Methoxyphenoxy)phenyl]piperazine

HRID 2353253Notes

Reaction equation

HRID 2353253 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[CH3:28][O:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][C:17]2[CH:16]=[CH:15][C:14]([N:11]3[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]3)=[CH:19][CH:18]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 1

HCID 57419565HCID 57419565, compound

Product 1

HCID 47387801-[4-(4-Methoxyphenoxy)phenyl]piperazineYield 78.5%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of the compound from step 2 (52 mg, 0.13 mmol), Pd(OH)2/C (20%, 5 mg) and methanol (3 mL) was stirred at ambient temperature under hydrogen (1 atm) for 24 h. The reaction mixture was filtered and the solvent was removed under vacuum to furnish the title compound (29 mg, 78.5%) as an off-white oil: MS (ESI) m/z 285 (M+H); 1H NMR (400 MHz, CDCl3) δ 2.31 (s, 3H), 3.12 (m, 4H), 3.16 (m, 4H), 6.85 (d, J=8.4 Hz, 2H), 6.89-6.95 (m, 4H), 7.11 (dd, J=0.8, 8.0 Hz, 2H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-4ee872af7a484100b32ba7a1cf0a53f0
Source dataset
uspto-grants-2010_07
Patent number
US07750012B2

Reaction notes

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