Piperidine → HCID 18686758, compound

HRID 1872496Notes

Reaction equation

HRID 1872496 reaction equation
Br[CH2:2][C:3]1[C:8]([Cl:9])=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=[CH:5][C:4]=1[Cl:13].C(N(CC)CC)C.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.CCOC(C)=O>C1COCC1>[Cl:9][C:8]1[C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:13])[C:3]=1[CH2:2][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

6

Reactant 4

HCID 8082PiperidineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 110115352,6-Dichloro-3-nitrobenzyl Bromide

Product 1

HCID 18686758HCID 18686758, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromomethyl-1,3-dichloro-4-nitro-benzene (20) (8.79 g, 30.8 mmol) and triethylamine (6.06 g, 60 mmol) in anhydrous THF (50 mL), piperidine (2.72 g, 32 mmol) was added at 0° C. under stirring. The reaction mixture was allowed to warm to room temperature gradually, and the reaction was monitored by TLC (SiO2, Hexanes:EtOAc, 1:1). After stirring for about 14 hours, the reaction mixture was evaporated to dryness, and the product was extracted in EtOAc (250 mL) and washed with water (2×100 mL) and dried (MgSO4). The product was purified by column chromatography (SiO2, hexanes:EtOAc 95:5 to 8:2) and was obtained as a yellow solid, yield: 7.38 g, 83%, mp 67-68° C. 1H-NMR (CDCl3) δ 1.37 (m, 2H), 1.46-1.49 (m, 4H), 2.45 (m, 4H), 3.7 (s, 2H); MS (CI) m/z 290 (M+H), 291 (M+2H). Anal Calc for C12H14Cl2N2O2 : C, 49.85; H, 4.88; N, 9.69. Found: C, 49.86; H, 4.88; N, 9.73.

Workup

  1. stirringAfter stirring for about 14 hours
  2. customthe reaction mixture was evaporated to dryness
  3. extractionthe product was extracted in EtOAc (250 mL)
  4. washwashed with water (2×100 mL)
  5. dry with materialdried (MgSO4)
  6. customThe product was purified by column chromatography (SiO2, hexanes:EtOAc 95:5 to 8:2)
  7. customwas obtained as a yellow solid, yield: 7.38 g, 83%, mp 67-68° C

Sources & evidence

ORD record
ord-8c3144a2d6514ac0862a6d5bff149af3
Source dataset
uspto-grants-2000_08
Patent number
US06110911

Reaction notes

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