Ethanol → 6-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridin-3-ylamine

HRID 42214

Reaction equation

[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].C(O)C>[Fe].O>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[N:25]=[CH:26][C:27]([NH2:30])=[CH:28][CH:29]=3)[CH2:22][CH2:23]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1-Benzyl-4-[4-(5-nitro-pyridin-2-yl)-piperazin-1-yl]-phthalazine (500 mg, 1.17 mmol), iron powder (523 mg, 9.38 mmol), ammonium chloride (125 mg, 0.234 mmol), ethanol (6 mL) and water (1.5 mL) are all combined in 50 mL round bottom flask with stir bar. The mixture is stirred and heated to 70° C. for 4 h. Material is filtered through a pad of Celite and washed with CH2Cl2. Concentrate to remove all ethanol and residual water. The residue is purified by flash chromatography on silica gel (0-18% MeOH/CH2Cl2) to afford the title compound (323 mg, 70%).

Workup

customall combined in 50 mL round bottom flask
stirringThe mixture is stirred
filtrationMaterial is filtered through a pad of Celite
washwashed with CH2Cl2
concentrationConcentrate
customto remove all ethanol and residual water
customThe residue is purified by flash chromatography on silica gel (0-18% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-1c09af0236714b09964a6dfb6776305b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536168B2

Linked notes

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