Hydrochloric Acid → 2-{N-[4-(1,1-Dioxido-2H-naphth[1,8-cd]isothiazol-2-yl)butyl]aminomethyl}-8-methoxytetralin

HRID 1081304Notes

Reaction equation

HRID 1081304 reaction equation
N[CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([O:12][CH3:13])[CH:6]=[CH:7][CH:8]=2)[CH2:3]1.[CH2:14]([N:16](CC)CC)C.Br[CH2:22][CH2:23][CH2:24][CH2:25][N:26]1[C:30]2[CH:31]=[CH:32][CH:33]=[C:34]3[CH:35]=[CH:36][CH:37]=[C:28]([C:29]=23)[S:27]1(=[O:39])=[O:38].[Cl-].[Na+].Cl>CN(C)C=O.C1(C)C=CC=CC=1>[O:38]=[S:27]1(=[O:39])[C:28]2=[CH:37][CH:36]=[CH:35][C:34]3=[CH:33][CH:32]=[CH:31][C:30](=[C:29]23)[N:26]1[CH2:25][CH2:24][CH2:23][CH2:22][NH:16][CH2:14][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[C:5]([O:12][CH3:13])[CH:6]=[CH:7][CH:8]=2)[CH2:3]1

Participants

8

Reactant 5

HCID 313Hydrochloric Acid2×HCID 5234Sodium ChlorideHCID 8471TriethylamineHCID 101979338-Methoxy-2-aminotetralinHCID 15057558HCID 15057558, compound

Product 1

HCID 224181432-{N-[4-(1,1-Dioxido-2H-naphth[1,8-cd]isothiazol-2-yl)butyl]aminomethyl}-8-methoxytetralin

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

1.6 g of 2-amino-8-methoxytetralin (8.4 mmol), 1.16 ml of triethylamine (8.4 mmol) and 1.59 g of 2-(4-bromobutyl)-2H-naphth[1,8-cd]isothiazole 1,1-dioxide are stirred for 48 h at 40° C. in 32 ml of dimethylformamide. The reaction solution is then stirred into a mixture of 320 ml of 5% strength sodium chloride solution, 100 ml of toluene, 8.4 ml of 1N hydrochloric acid and kieselguhr. The kieselguhr containing the hydrochloride of the final product attached thereto is filtered off with suction-- and introduced into a mixture of 300 ml of water and 100 ml of toluene. The final product is transferred to the organic phase by dropwise addition of 9 ml of 1N sodium hydroxide solution.

Sources & evidence

ORD record
ord-714b0a0038fe4d65b811d668d6cc3d05
Source dataset
uspto-grants-1996_12
Patent number
US05585392

Reaction notes

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