4-Methylpiperidine → 1-(2-Chloro-4-nitrobenzyl)-4-methylpiperidine

HRID 735118Notes

Reaction equation

HRID 735118 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[CH3:13][CH:14]1[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:6][C:3]=1[CH2:4][N:17]1[CH2:18][CH2:19][CH:14]([CH3:13])[CH2:15][CH2:16]1

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 3016511alpha,2-Dichloro-4-nitrotoluene

Product 1

HCID 688165431-(2-Chloro-4-nitrobenzyl)-4-methylpiperidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1 g (4.85 mmol) of 2-chloro-4-nitrobenzylchloride is slowly added dropwise to 2 mL (16.22 mmol) of 4-methylpiperidine at ambient temperature and the mixture is stirred for 15 minutes. The reaction mixture is diluted with ethyl acetate and extracted twice with water. The organic phase is dried over sodium sulfate and evaporated down. Yield: 1.3 g (99.7% of theory); C13H17ClN2O2 (M=268.74); calc.: molecular ion peak (M+H)+: 269/271; found: molecular ion peak (M+H)+: 269/271; Rf value: 0.4 (Alox, petroleum ether).

Workup

  1. extractionextracted twice with water
  2. dry with materialThe organic phase is dried over sodium sulfate
  3. customevaporated down

Sources & evidence

ORD record
ord-68fe302d281a4c348e1ddba06fb81b3a
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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