Sulfuric Acid → HCID 70033087, compound

HRID 1862060Notes

Reaction equation

HRID 1862060 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.[S:34](=[O:38])(=[O:37])([OH:36])[OH:35]>O1CCCC1>[S:34]([OH:38])([OH:37])(=[O:36])=[O:35].[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 1118Sulfuric AcidHCID 9846516AR-A000002

Product 1

HCID 70033087HCID 70033087, compoundYield 31%

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 (2 mL) by heating and sulfuric acid (25 mg, 0.24 mmol), dissolved in tetrahydrofuran (1 mL), was added dropwise. The white precipitate was filtered and washed with tetrahydrofuran to give 110 mg (89% yield). The crude salt (80 mg) was recrystallized from HBO (12 mL) and allowed to stand in the refrigerator over night. The solid was filtered and washed with cold H2O to give 28 mg (31% yield) a white solid: rmp 230° C. (decom.). Anal. Calcd. for C27H36N4O2xH2O4SxH2O: C, 57.4; H, 7.1; N, 9.9. Found: C, 57.7; H, 7.4; N, 9.9.

Workup

  1. temperatureby heating
  2. additionwas added dropwise
  3. filtrationThe white precipitate was filtered
  4. washwashed with tetrahydrofuran
  5. customto give 110 mg (89% yield)
  6. customThe crude salt (80 mg) was recrystallized from HBO (12 mL)
  7. waitto stand in the refrigerator over night
  8. filtrationThe solid was filtered
  9. washwashed with cold H2O

Sources & evidence

ORD record
ord-775d8073ccc841ca9e69ac459bc35260
Source dataset
uspto-grants-2003_03
Patent number
US06534652B2

Reaction notes

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