Water → (R)-N-[5-Methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide Benzenesulfonate

HRID 427351Notes

Reaction equation

HRID 427351 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]1([S:40]([OH:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(OCC)C.O>O1CCCC1>[C:34]1([S:40]([OH:43])(=[O:42])=[O:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.[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

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 7371Benzenesulfonic AcidHCID 9846516AR-A000002

Product 1

HCID 86584031(R)-N-[5-Methyl-8-(4-methylpiperazin-1-yl)-1,2,3,4-tetrahydro-2-naphthyl]-4-morpholinobenzamide Benzenesulfonate

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 benzenesulfonic acid (40 mg, 0.24 mmol), dissolved in tetrahydrofuran (4 mL), was added dropwise. Diethyl ether was added and the resulting oil was titurated. The solid was filtered and washed with diethyl ether to give a white solid that was stored in an exicator over blue gel: mp >250° C. Anal. Calcd. for C27H36N4O2×C6H6O3S×H2O: 63.4; H, 6.8; N, 9.0. Found: C, 63.1; H, 7.0; N, 8.7.

Workup

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

Sources & evidence

ORD record
ord-4d7831aed1984afc9a2abe54cf9b5b02
Source dataset
uspto-grants-2001_11
Patent number
US06313118B1

Reaction notes

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