Morpholine → 4-(4-Nitro-3-piperidin-1-ylphenyl)morpholine

HRID 646843Notes

Reaction equation

HRID 646843 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([N:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH:7]=1.[NH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>O>[N+:14]([C:5]1[CH:4]=[CH:3][C:2]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:7][C:6]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([O-:16])=[O:15]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 30960791-(5-Chloro-2-nitrophenyl)piperidine

Product 1

HCID 43734724-(4-Nitro-3-piperidin-1-ylphenyl)morpholineYield 89.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 150 mg (0.623 mmol) 1-(5-chloro-2-nitro-phenyl)-piperidine (as prepared in the previous step) and 272 μL (3.12 mmol) of morpholine were heated with stirring under Ar at 125° C. for 84 h. After cooling to rt, the mixture was poured into water (40 mL) and extracted with EtOAc (2×20 mL). The combined extracts were washed with water (2×10 mL) and brine (10 mL) and then dried (Na2SO4) Concentration afforded 162 mg (89%) of the title compound as an orange resin: Mass spectrum (ESI, m/z): Calcd. for C15H21N3O3, 292.2 (M+H), found 292.1.

Workup

  1. temperaturewere heated
  2. temperatureAfter cooling to rt
  3. extractionextracted with EtOAc (2×20 mL)
  4. washThe combined extracts were washed with water (2×10 mL) and brine (10 mL)
  5. customdried
  6. concentration(Na2SO4) Concentration

Sources & evidence

ORD record
ord-77374ba2cc694152bdb264980e236783
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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