Ammonium Hydroxide → 2-(4-Cyclopropylpiperazin-1-yl)benzooxazole

HRID 1944700Notes

Reaction equation

HRID 1944700 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][C:16](C#N)=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[NH4+].[OH-]>CO.C1COCC1.[Ni]>[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[O:11][C:12]4[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=4[N:14]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 237288972-(4-Cyclopropylpiperazin-1-yl)benzooxazole-5-carbonitrile

Product 1

HCID 474536642-(4-Cyclopropylpiperazin-1-yl)benzooxazoleYield 111.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-(4-cyclopropylpiperazin-1-yl)benzooxazole-5-carbonitrile (500 mg, 1.85 mmol) in MeOH-THF (12 mL, 5:3) was added NH4OH (1.5 mL) and Raney Ni (100 mg). The mixture was stirred for 12 h at rt under a H2 atmosphere. After filtration, the mixture was concentrated to give 5-aminomethyl-[2-(4-cyclopropylpiperazin-1-yl)benzooxazole (500 mg, 99%), which was used in the next step without further purification.

Workup

  1. filtrationAfter filtration
  2. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-209de00905cf4560a0538d5b6b7a9481
Source dataset
uspto-grants-2013_03
Patent number
US08394842B2

Reaction notes

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