1-Chloro-2-nitrobenzene → N-[2-(1,2,3,5,6,7-hexahydropyrrolizin-8-yl)ethyl]-2-nitroaniline

HRID 260924Notes

Reaction equation

HRID 260924 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[NH2:11][CH2:12][CH2:13][C:14]12[CH2:21][CH2:20][CH2:19][N:18]1[CH2:17][CH2:16][CH2:15]2>>[N:18]12[CH2:19][CH2:20][CH2:21][C:14]1([CH2:13][CH2:12][NH:11][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9])[CH2:15][CH2:16][CH2:17]2

Participants

3

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 107969772-(Hexahydro-1H-pyrrolizin-7a-yl)ethanamine

Product 1

HCID 178115N-[2-(1,2,3,5,6,7-hexahydropyrrolizin-8-yl)ethyl]-2-nitroaniline

Procedure

The procedures described in Example 12 were repeated except that 1-chloro-2-nitrobenzene (2.04 g, 12.9 mmol) and 5-(2-aminoethyl)-1-azabicyclo[3.3.0]octane (4.00 g, 25.9 mmol) were employed. In this case, the desired compound was obtained as a orange liquid (3.32 g, 98.54%).

Sources & evidence

ORD record
ord-93d16f750d3d430f9f19a5a0c842329e
Source dataset
uspto-grants-1996_06
Patent number
US05530138

Reaction notes

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