1-Methylpiperazine → 2-Tert-butyl-6-[(4-methylpiperazin-1-yl)thiocarbonylamino]-5-(4-methylpiperidin-1-yl)benzothiazole

HRID 5784Notes

Reaction equation

HRID 5784 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].[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C(Cl)Cl>[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([NH:14][C:15]([N:28]3[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]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 531671-MethylpiperazineHCID 156103622-Tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole

Product 1

HCID 197941982-Tert-butyl-6-[(4-methylpiperazin-1-yl)thiocarbonylamino]-5-(4-methylpiperidin-1-yl)benzothiazoleYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 90 g of 2-tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole in 900 ml of methylene chloride is added dropwise 26 g of N-methylpiperazine. The solution is stirred for 1 hour, washed with water, dried over anhydrous sodium sulphate and evaporated to give 110 g of 2-tert-butyl-6-[(4-methylpiperazin-1-yl)thiocarbonylamino]-5-(4-methylpiperidin-1-yl)benzothiazole, melting at 192°-195° C.

Workup

  1. washwashed with water
  2. dry with materialdried over anhydrous sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-9fc75b912d0046a3a872e761ace84d22
Source dataset
uspto-grants-1993_09
Patent number
US05246927

Reaction notes

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