Water → HCID 9964710, compound

HRID 349661Notes

Reaction equation

HRID 349661 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.[OH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]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][CH:13]([OH:12])[CH2:14][CH2:15]2)[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 742185-Chloro-2-nitroanilineHCID 79341Piperidin-4-ol

Product 1

HCID 9964710HCID 9964710, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 5-chloro-2-nitrophenylamine (1.3 g, 7.0 mmol), 4-hydroxypiperidine (2.2 g, 20 mmol), and K2CO3 (1.0 g, 7 mmol) in DMF (20 mL) was stirred at 120° C. for 18 h. The reaction mixture was cooled to room temperature, poured into water (50 mL) and extracted with EtOAc (3×50 mL). The combined organic extracts were dried over sodium sulfate, concentrated in vacuo, and the oily residue was triturated with 70/30 EtOAc/CHCl3 (8 mL) to yield a yellow solid. The solid product was collected by filtration, washed with 70:30 EtOAc/CHCl3 (8 mL), and dried in vacuo (0.63 g, 38%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionextracted with EtOAc (3×50 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customthe oily residue was triturated with 70/30 EtOAc/CHCl3 (8 mL)
  6. customto yield a yellow solid
  7. filtrationThe solid product was collected by filtration
  8. washwashed with 70:30 EtOAc/CHCl3 (8 mL)
  9. customdried in vacuo (0.63 g, 38%)

Sources & evidence

ORD record
ord-6cb96f32dbd34ed2b8034d842b2b3c1f
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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