1-Fluoro-3-nitrobenzene → tert-Butyl 4-(3-aminophenyl)piperazine-1-carboxylate

HRID 1989052Notes

Reaction equation

HRID 1989052 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[CH:3]=1.[C:11]([N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>>[C:14]([O:13][C:11]([N:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[CH:3]=2)[CH2:20][CH2:19]1)=[O:12])([CH3:17])([CH3:15])[CH3:16]

Participants

3

Reactant 2

HCID 98231-Fluoro-3-nitrobenzeneHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22330182tert-Butyl 4-(3-aminophenyl)piperazine-1-carboxylate

Procedure

Using the procedure outlined in Example 37 (A), the title compound was prepared from 1-fluoro-3-nitrobenzene (Ig, 7 mmol) and 1-Boc-piperazine (1.9 g, 10 mmol) 1H NMR (400 MHz, CDCl3) δ (ppm): 7.03 (t, J=8.0 Hz, 1H), 6.34 (d, J=8.2 Hz, 1H), 6.23 (m, 2H), 3.62 (br, 2H), 3.53 (m, 4H), 3.07 (m, 2H), 1.47 (s, 9H).

Sources & evidence

ORD record
ord-3e3c4eec05144d7aa6fa6e5666fe0844
Source dataset
uspto-grants-2010_01
Patent number
US07642270B2

Reaction notes

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