L-Malic Acid → (R)-N-[5-Methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide Hydrogen (S)-Malate

HRID 427356Notes

Reaction equation

HRID 427356 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH2:4][CH2:5][C@@H:6]([NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=1)[CH2:7]2.[CH2:34]([C:40]([OH:42])=[O:41])[C@H:35]([OH:39])[C:36]([OH:38])=[O:37]>O1CCCC1>[C:36]([OH:38])(=[O:37])[C@H:35]([CH2:34][C:40]([OH:42])=[O:41])[OH:39].[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[C:8]2[C:3]=1[CH2:4][CH2:5][C@@H:6]([NH:19][C:20](=[O:33])[C:21]1[CH:26]=[CH:25][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[CH:23][CH:22]=1)[CH2:7]2

Participants

4

Reactant 2

HCID 222656L-Malic AcidHCID 9846516AR-A000002

Product 1

HCID 131722954(R)-N-[5-Methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide Hydrogen (S)-MalateYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

(R)-N-[5-Methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide (100 mg, 0.22 mmol) was dissolved in tetrahydrofuran (20 mL) and L-(−)-malic acid (59 mg, 0.44 mmol), dissolved in tetrahydrofuran (3 mL), was added dropwise. The precipitate was filtered and the solid material was recrystallized from a 15% H2O in acetone solution (7 mL). The solid was filtered to give 100 mg (77% yield) of white crystals: mp 200° C. (decom.). Anal. Calcd. for C27H36N4O2×C4H6O5×2H2O: C, 57.9; H, 7.6; N, 9.7. Found: C, 58.1; H, 7.4; N, 9.6.

Workup

  1. additionwas added dropwise
  2. filtrationThe precipitate was filtered
  3. customthe solid material was recrystallized from a 15% H2O in acetone solution (7 mL)
  4. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-b9296e7b9d0f4a219da1952470aec2ad
Source dataset
uspto-grants-2001_11
Patent number
US06313118B1

Reaction notes

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