Water → 1-(3-Amino-4-nitrophenyl)-piperidin-3-ol

HRID 349665Notes

Reaction equation

Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.Cl.[OH:13][CH:14]1[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[NH2:8][C:6]1[CH:7]=[C:2]([N:16]2[CH2:17][CH2:18][CH2:19][CH:14]([OH:13])[CH2:15]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (1.3 g, 7.0 mmol), 3-hydroxypiperidine hydrochloride (3.0 g, 20 mmol), and K2CO3 (3.0 g, 22 mmol) in DMF (10 mL) was stirred at 120° C. for 18 h. The reaction mixture was cooled to room temperature, poured into water (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 50:50 CHCl3/EtOAc) to yield the product as an orange solid (0.89 g, 54%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionextracted with EtOAc (3×100 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
custompurified by flash chromatography (silica gel, 4×7.5 cm, eluted with 50:50 CHCl3/EtOAc)

Sources & evidence

ORD record: ord-a92c290757544884bc881a22da7b455b
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179912B2

Reaction notes

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