Citric Acid → HCID 70032629, compound

HRID 427357Notes

Reaction equation

HRID 427357 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:46])(=[O:45])[CH2:35][C:36]([CH2:41][C:42]([OH:44])=[O:43])([C:38]([OH:40])=[O:39])[OH:37]>O1CCCC1.O>[C:34]([OH:46])(=[O:45])[CH2:35][C:36]([CH2:41][C:42]([OH:44])=[O:43])([C:38]([OH:40])=[O:39])[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

5

Reactant 2

HCID 311Citric AcidHCID 9846516AR-A000002

Product 1

HCID 70032629HCID 70032629, compoundYield 62.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 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 (15 mL) and citric acid (51 mg, 0.27 mmol), dissolved in 10% H2O in tetrahydrofuran (5 mL), was added dropwise. The solid material was filtered and recrystallized from a 20% H2O in ethanol (5 mL). The solid was filtered to give 88 mg (62% yield) of white crystals: mp 160 ° C. (decom.). Anal. Calcd. for C27H36N4O2×C6H8O7×2H2O: 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 solid material was filtered
  3. customrecrystallized from a 20% H2O in ethanol (5 mL)
  4. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-e428df5bafdf4912bdac7271662d5b87
Source dataset
uspto-grants-2001_11
Patent number
US06313118B1

Reaction notes

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