Salicylic Acid → HCID 20653153, compound

HRID 1596194Notes

Reaction equation

HRID 1596194 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.[C:34]([OH:43])(=[O:42])[C:35]1[C:36](=[CH:38][CH:39]=[CH:40][CH:41]=1)[OH:37]>C(O)C>[C:34]([OH:43])(=[O:42])[C:35]1[C:36](=[CH:38][CH:39]=[CH:40][CH:41]=1)[OH:37].[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 338Salicylic AcidHCID 9846516AR-A000002

Product 1

HCID 20653153HCID 20653153, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a boiling solution of (R)-N-[5-methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide (1.0 g, 2.2 mmol) in ethanol (50 mL) was added a solution of salicylic acid (400 mg, 2.9 mmol) in ethanol (10 mL). The solvent was concentrated in vacuo and the remaining solution (20 mL) was allowed to cool to room temperature. The solution was put in the freezer over the weekend. The crystals were filtered and dried in vacuo to give 1.2 gram (86% yield) of the title compound as white crystals: mp 235-240° C. Anal. Calcd. for C27H36N4O2×C7H6O3: C, 69.6; H, 7.2; N, 9.6. Found: C, 69.5; H, 7.2; N, 9.5.

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. filtrationThe crystals were filtered
  3. customdried in vacuo

Sources & evidence

ORD record
ord-3357bcbc8d2b4fdaa100929d1644f411
Source dataset
uspto-grants-2001_09
Patent number
US06291458B1

Reaction notes

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