alpha-Bromo-2-nitrotoluene → tert-Butyl 4-(1-methoxy-3-(2-nitrophenyl)-1-oxopropan-2-yl)piperazine-1-carboxylate

HRID 132205Notes

Reaction equation

HRID 132205 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[N+:19]([C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]Br)([O-:21])=[O:20].COC(=O)C(C1CCN(C(OC(C)(C)C)=O)CC1)CC1C=CC=CC=1[N+]([O-])=O>>[CH3:1][O:2][C:3](=[O:18])[CH:4]([N:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH2:7][CH2:6]1)[CH2:24][C:23]1[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=1[N+:19]([O-:21])=[O:20]

Participants

4

Reactant 3

HCID 77569alpha-Bromo-2-nitrotolueneHCID 46785870Tert-butyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylateHCID 59732041Tert-butyl 4-(1-methoxy-3-(2-nitrophenyl)-1-oxopropan-2-yl)piperidine-1-carboxylate

Product 1

HCID 59732018tert-Butyl 4-(1-methoxy-3-(2-nitrophenyl)-1-oxopropan-2-yl)piperazine-1-carboxylateYield 51%

Procedure

tert-Butyl 4-(2-methoxy-2-oxoethyl)piperazine-1-carboxylate (1.0 g, 3.9 mmol) and 2-nitrobenzylbromide (1.0 g, 4.6 mmol) were reacted in a manner analogous to the preparation of tert-butyl 4-(1-methoxy-3-(2-nitrophenyl)-1-oxopropan-2-yl)piperidine-1-carboxylate. Title compound was obtained as amber oil in 51% yield. MS m/e (M+H)+=394.4.

Sources & evidence

ORD record
ord-3b2dc3ebc34e4e8ba164868d00eb64e8
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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