Piperazine → 2-Tert-butyl-5-(4-methyl-piperidin-1-yl)-6-[(piperazin-1-yl)thiocarbonylamino]benzothiazole

HRID 5793Notes

Reaction equation

HRID 5793 reaction equation
[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([N:14]=[C:15]=[S:16])[C:11]([N:17]3[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1>C(Cl)(Cl)Cl>[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([NH:14][C:15]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[S:16])[C:11]([N:17]3[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:10][C:8]=2[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 156103622-Tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole

Product 1

HCID 543745932-Tert-butyl-5-(4-methyl-piperidin-1-yl)-6-[(piperazin-1-yl)thiocarbonylamino]benzothiazoleYield 69.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 3.45 g of 2-tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole, described in Example 1, and 8.6 g of anhydrous piperazine in 30 ml of chloroform is stirred for 3 hours, washed with water, dried over anhydrous sodium sulphate and evaporated to get a sticky residue which is triturated with isopropanol and filtered to obtain 3 g of 2-tert-butyl-5-(4-methyl-piperidin-1-yl)-6-[(piperazin-1-yl)thiocarbonylamino]benzothiazole, melting at 278°-281°.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulphate
  3. customevaporated
  4. customto get a sticky residue which
  5. customis triturated with isopropanol
  6. filtrationfiltered

Sources & evidence

ORD record
ord-0021d0cc1d434e90be2099cbc1a36c49
Source dataset
uspto-grants-1993_09
Patent number
US05246927

Reaction notes

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