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Ammonium Hydroxide → 6-Aminomethyl-2-(4-cyclopropylpiperazin-1-yl)benzothiazole

HRID 1619254
Notes
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Reaction equation

HRID 1619254 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]4[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[NH4+].[OH-]>CO.C1COCC1.[Ni]>[NH2:20][CH2:19][C:17]1[CH:16]=[CH:15][C:13]2[N:14]=[C:10]([N:7]3[CH2:8][CH2:9][N:4]([CH:1]4[CH2:2][CH2:3]4)[CH2:5][CH2:6]3)[S:11][C:12]=2[CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 595887892-(4-Cyclopropylpiperazin-1-yl)benzothiazole-6-carbonitrile

Product 1

HCID 595887836-Aminomethyl-2-(4-cyclopropylpiperazin-1-yl)benzothiazoleYield 49.3%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzothiazole-6-carbonitrile (1 g, 3.52 mmol) in MeOH-THF (120 mL, 5:3) was added NH4OH (15 mL) and Raney Ni (200 mg). The mixture was stirred for 12 h at rt under 50 psi H2 atmosphere. After filtration, the mixture was concentrated to give 6-aminomethyl-2-(4-cyclopropylpiperazin-1-yl)benzothiazole (500 mg, 49.3%), which was used in the next step without further purification.

Workup

  1. filtrationAfter filtration
  2. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-1ac1f4da87ba4a64a2cb7837c239744f
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772285B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes