1-Methyl-4-(2-nitroethenyl)benzene → 1-Butyl-3-p-tolyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine

HRID 599886Notes

Reaction equation

HRID 599886 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH3:15][C:16]1[CH:21]=[CH:20][C:19]([CH:22]=[CH:23][N+:24]([O-])=O)=[CH:18][CH:17]=1>C(N)CCC>[CH2:9]([N:24]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:13][C:12]=2[C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH3:15])=[CH:17][CH:18]=2)=[CH:23]1)[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 2

HCID 2867351-Methyl-4-(2-nitroethenyl)benzeneHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 111615141-Butyl-3-p-tolyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridineYield 77.6%

Reagents, catalysts & solvents 1

HCID 8007ButylamineSolvent

Procedure

The title compound (292.8 mg) was prepared from 0.56 g of 4-oxo-piperidine-1-carboxylic acid tert-butyl ester, 260 μL of butylamine, and 0.45 g of 1-methyl-4-(2-nitro-vinyl)-benzene. MS (ESI): exact mass calculated for C18H24N2, 268.19; found, m/z 269.2 [M+H]+. 1H NMR (500 MHz, CD3OD): 7.20-7.14 (m, 4H), 6.93 (s, 1H), 4.32 (s, 2H), 3.88 (t, J=7.1 Hz, 2H), 3.56 (t, J=6.0 Hz, 2H), 3.00 (t, J=6.0 Hz, 2H), 2.32 (s, 3H), 1.77-1.70 (m, 2H), 1.41-1.33 (m, 2H), 0.97 (t, J=7.4 Hz, 3H).

Sources & evidence

ORD record
ord-22476dd9a5c241c19e515451715dab1d
Source dataset
uspto-grants-2011_03
Patent number
US07897771B2

Reaction notes

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