HCID 67182318, compound → HCID 46199224, compound

HRID 1966467Notes

Reaction equation

HRID 1966467 reaction equation
C([N:8]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:9]1[CH:10]=[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:25])[CH2:20][CH2:19]2)[CH:12]=[CH:13][C:14]=1[N:15]([CH3:17])[CH3:16])C1C=CC=CC=1>C(O)C.[Pd]>[CH3:16][N:15]([CH3:17])[C:14]1[CH:13]=[CH:12][C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[O:25])[CH2:20][CH2:19]2)=[CH:10][C:9]=1[NH:8][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 1

HCID 67182318HCID 67182318, compound

Product 1

HCID 46199224HCID 46199224, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

To a stirred solution of (4-(3-(benzyl(phenyl)amino)-4-(dimethylamino)phenyl)piperazin-1-yl)(phenyl)methanone (0.49 g, 1 mmol) in ethanol (10 ml), 10% Pd—C was added under argon. The resulting mixture was stirred under H2 atmosphere at room temperature for 10 h. After completion of reaction (by TLC) it was filtered through celite, evaporated under vacuum to get the crude product. Flash chromatography gave (4-(4-(dimethylamino)-3-(phenylamino)phenyl)piperazin-1-yl)(phenyl)methanone which was isolated finally as trihydrochloride salt (0.39 g), 86% yield. 1H NMR (500 MHz, DMSO): δ 3.26 (s, 6H), 3.4 (bs, 4H), 4.2 (bs, 2H), 4.4 (s, 2H), 7.15 (t, J=7, 7.5 Hz 2H), 7.26 (d, J=7.6 Hz 2H), 7.29 (s, 2H), 7.42 (t, J=7.5, 8 Hz, 2H), 7.51 (m, 7H).

Workup

  1. customAfter completion of reaction (by TLC) it
  2. filtrationwas filtered through celite
  3. customevaporated under vacuum
  4. customto get the crude product

Sources & evidence

ORD record
ord-cf2d7d4fd98a40ac86834e1f5156d88f
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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