Piperidine → 1-(2-Methyl-6-nitrophenyl)piperidine

HRID 32905

Reaction equation

Cl[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1>>[CH3:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

Reactant 2

HCID 8082Piperidine

HCID 775912-Chloro-3-nitrotoluene

Product 1

HCID 127982131-(2-Methyl-6-nitrophenyl)piperidineYield 35%

Procedure

Using a procedure similar to Example 8, step (a), 2-chloro-3-methylnitrobenzene (264 mg, 1.53 mmol) was heated to 110° C. overnight in 3 mL of piperidine to afford 128 mg (35%) of the title compound and an undetermined amount of starting material. 1H-NMR (CDCl3; 400 MHz): δ 7.41-7.34 (m, 2H), 7.02 (t, 1H, J=7.7 Hz), 2.96-2.93 (m, 4H), 2.36 (s, 3H), 1.65 (br s, 6H).

Sources & evidence

ORD record: ord-be105cc7411f4b82a395347f5ce226f9
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427683B2

Linked notes

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