Diethyl Ether → (R)-N-[5-Methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide Hydrogen 1,2-Ethanedisulfonate

HRID 427352Notes

Reaction equation

HRID 427352 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.O.O.[CH2:36]([S:42]([OH:45])(=[O:44])=[O:43])[CH2:37][S:38]([OH:41])(=[O:40])=[O:39].C(OCC)C>O1CCCC1>[CH2:36]([S:42]([OH:45])(=[O:44])=[O:43])[CH2:37][S:38]([OH:41])(=[O:40])=[O: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

5

Reactant 3

HCID 3283Diethyl EtherHCID 9846516AR-A000002HCID 57346009Ethane-1,2-disulfonic acid--water (1/2)

Product 1

HCID 86584032(R)-N-[5-Methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide Hydrogen 1,2-Ethanedisulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (3 mL) by heating and 1,2-ethanedisulfonic acid dihydrate (55 mg, 0.24 mmol), dissolved in tetrahydfofuran (2 mL), was added dropwise. Diethyl ether (2 mL) was added, the solid was filtered and washed with tetrahydrofuran/diethyl ether to give a white solid that was stored in an exicator over blue gel: mp 220° C. (decom.). Anal. Calcd. for C27H36N4O2×C2H6O6S2×4H2O: C, 48.9; H, 7.1; N, 7.9. Found: C, 49.1; H, 6.8;N, 7.6.

Workup

  1. temperatureby heating
  2. additionwas added dropwise
  3. filtrationthe solid was filtered
  4. washwashed with tetrahydrofuran/diethyl ether
  5. customto give a white solid

Sources & evidence

ORD record
ord-e3053b2cd57445dd9e307e4cc4bc8676
Source dataset
uspto-grants-2001_11
Patent number
US06313118B1

Reaction notes

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