Ammonium Hydroxide → 2-(4-Isopropylpiperazin-1-yl)benzothiazole

HRID 1944692Notes

Reaction equation

HRID 1944692 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][C:16](C#N)=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[NH4+].[OH-]>CO.C1COCC1.[Ni]>[CH:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[S:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:8][CH2:9]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 237288942-(4-Isopropylpiperazin-1-yl)benzothiazole-5-carbonitrile

Product 1

HCID 106114582-(4-Isopropylpiperazin-1-yl)benzothiazoleYield 110.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-(4-isopropylpiperazin-1-yl)benzothiazole-5-carbonitrile (500 mg, 1.75 mmol) in MeOH-THF (66 mL, 3:5) was added NH4OH (7 mL) and Raney Ni (100 mg). The mixture was stirred for 12 h at rt under a H2 atmosphere. The mixture was filtered and the filtrate was concentrated to give 5-aminomethyl-[2-(4-isopropylpiperazin-1-yl)benzothiazole 507 mg (100%), which was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-230b611d795d4f46b595b50b1e53c080
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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