N-Ethylaniline → HCID 20081641, compound

HRID 1609461Notes

Reaction equation

HRID 1609461 reaction equation
Cl[C:2]1[N:7]([CH2:8][CH3:9])[C:6]2[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=2[S:4](=[O:15])(=[O:14])[N:3]=1.C(NC1C=CC=CC=1)C.[N:25]1([CH2:31][C:32]2[CH:33]=[C:34]([CH:62]=[CH:63][CH:64]=2)[O:35][CH2:36][CH2:37][CH2:38][N:39]([CH2:53][C:54]2[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][CH:55]=2)C2N(C)C3C=CC=CC=3S(=O)(=O)N=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>C(Cl)(Cl)Cl>[N:25]1([CH2:31][C:32]2[CH:33]=[C:34]([CH:62]=[CH:63][CH:64]=2)[O:35][CH2:36][CH2:37][CH2:38][N:39]([CH2:53][C:54]2[CH:59]=[CH:58][C:57]([O:60][CH3:61])=[CH:56][CH:55]=2)[C:2]2[N:7]([CH2:8][CH3:9])[C:6]3[CH:10]=[CH:11][CH:12]=[CH:13][C:5]=3[S:4](=[O:15])(=[O:14])[N:3]=2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 7670N-EthylanilineHCID 1986914H-1,2,4-Benzothiadiazine, 3-chloro-4-ethyl-, 1,1-dioxideHCID 15231589HCID 15231589, compound

Product 1

HCID 20081641HCID 20081641, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 0.8 g quantity of 3-chloro-4-ethyl-1,2,4-benzothiadiazine-1,1-dioxide in the form of white crystals prepared in the same manner as in Reference Example 4 with the exception of using N-ethylaniline in place of N-methylaniline was added to a solution of 1.2 g of the N-[3-[3-(piperidinomethyl)phenoxy]propyl]-4'-methoxybenzylamine obtained in Example 1, (iii) in 12 ml of chloroform, and the mixture was stirred at room temperature for 8 hours. The reaction mixture was purified in the same manner as in Example 1, giving 1.67 g of 3-[N-[3-[3-(piperidinomethyl)phenoxy]-propyl]-4'-methoxybenzylamino]-4-ethyl-1,2,4-benzothiadiazine-1,1-dioxide (yield 88% ). This compound was converted to an oxalic acid salt in the same manner as in Example 1 to obtain 1.81 g of a compound 15 in the form of white crystals as listed in Table 1 (yield 92% ). M.p.: 85°~90° C.

Workup

  1. customThe reaction mixture was purified in the same manner as in Example 1

Sources & evidence

ORD record
ord-967be979e3844abdb675b3fdccb8aece
Source dataset
uspto-grants-1995_03
Patent number
US05401739

Reaction notes

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