2-Tert-butyl-5-(4-methylpiperidin-1-yl)-6-nitrobenzothiazole → 6-Amino-2-tert-butyl-5-(4-methylpiperidin-1-yl)benzothiazole

HRID 5786Notes

Reaction equation

HRID 5786 reaction equation
[C:1]([C:5]1[S:6][C:7]2[CH:13]=[C:12]([N+:14]([O-])=O)[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]>CO.[Ni]>[NH2:14][C:12]1[C:11]([N:17]2[CH2:22][CH2:21][CH:20]([CH3:23])[CH2:19][CH2:18]2)=[CH:10][C:8]2[N:9]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[S:6][C:7]=2[CH:13]=1

Participants

4

Reactant 1

HCID 197941892-Tert-butyl-5-(4-methylpiperidin-1-yl)-6-nitrobenzothiazole

Product 1

HCID 197941866-Amino-2-tert-butyl-5-(4-methylpiperidin-1-yl)benzothiazole

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 15.2 g of 2-tert-butyl-5-(4-methyl-piperidin-1-yl)-6-nitrobenzothiazole in 600 ml of methanol is hydrogenated in presence of 6.5 g of Raney Nickel at room temperature. After removing the catalyst the solution is concentrated and the solid filtered to give 6-amino-2-tert-butyl-5-(4-methylpiperidin-1-yl)benzothiazole melting at 146°-148°.

Workup

  1. customAfter removing the catalyst the solution
  2. concentrationis concentrated
  3. filtrationthe solid filtered

Sources & evidence

ORD record
ord-d2d2589cd1d140879dce79874d0e6100
Source dataset
uspto-grants-1993_09
Patent number
US05246927

Reaction notes

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