Hydrochloric Acid → HCID 15057539, compound

HRID 1081303Notes

Reaction equation

HRID 1081303 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:13][CH3:14])[CH:7]=[CH:8][CH:9]=2)[CH2:4]1.C(N(CC)CC)C.Br[CH2:23][CH2:24][CH2:25][CH2:26][N:27]1[C:31](=[O:32])[C:30]2[CH:33]=[CH:34][CH:35]=[CH:36][C:29]=2[S:28]1(=[O:38])=[O:37].[Cl-].[Na+].Cl>CN(C)C=O.C1(C)C=CC=CC=1>[O:37]=[S:28]1(=[O:38])[C:29]2[CH:36]=[CH:35][CH:34]=[CH:33][C:30]=2[C:31](=[O:32])[N:27]1[CH2:26][CH2:25][CH2:24][CH2:23][NH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:13][CH3:14])[CH:7]=[CH:8][CH:9]=2)[CH2:4]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 8471Triethylamine2×HCID 107817741,1-Dioxido-2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-oneHCID 15057535HCID 15057535, compound

Product 1

HCID 15057539HCID 15057539, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

0.95 g of 2-aminomethyl-8-methoxytetralin (5 mmol), 0.70 ml of triethylamine (5mmol) and 1.59 g of 2-(4-bromobutyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide (5 mmol) are stirred at 40° C for 24 h in 19 ml of dimethylformamide. The reaction solution is then stirred into a mixture of 190 ml of 5% strength sodium chloride solution, 60 ml of toluene and 5 ml of 1N hydrochloric acid. After the organic phase has been separated off, the aqueous phase containing the final product precipitated as the resinous hydrochloride is stirred with 60 ml of toluene and 7 ml of triethylamine (50 mmol). The organic phase is separated off again, washed until neutral with water and dried over sodium sulphate. The solvent is distilled off in vacuo. The residue is chromatographed on silica gel 60 (Merck). Toluene/methanol 85:15 is in this case used as the eluent. The main fractions contain the two final products as yellow, viscous oils.

Workup

  1. customAfter the organic phase has been separated off
  2. additionthe aqueous phase containing the final product
  3. customprecipitated as the resinous hydrochloride
  4. customThe organic phase is separated off again
  5. washwashed until neutral with water
  6. dry with materialdried over sodium sulphate
  7. distillationThe solvent is distilled off in vacuo
  8. customThe residue is chromatographed on silica gel 60 (Merck)

Sources & evidence

ORD record
ord-4f38a18604d044a39d087a33d49816d6
Source dataset
uspto-grants-1996_12
Patent number
US05585392

Reaction notes

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