p-Fluoronitrobenzene → tert-Butyl 4-(4-nitrophenyl)-1,4-diazepane-1-carboxylate

HRID 1509868Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[C:11]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[C:11]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][N:21]([C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=2)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

Participants

Conditions

Temperature: 100 °C

Procedure

This compound was prepared in a similar way as described in literature (Journal of Medicinal Chemistry (2005), 48, 2371). A mixture of 1-fluoro-4-nitro-benzene (2.06 g, 14.7 mmol), [1,4]Diazepane-1-carboxylic acid tert-butyl ester (3.52 g, 17.6 mmol) and potassium carbonate (4.85 g, 35.2 mmol) in DMF (100 mL) was heated to 100° C. and stirred for 2 h. The reaction mixture was diluted with EtOAc (100 mL) and washed with water (100 mL), brine (50 mL), dried with anhydrous sodium sulfate and the solvent was removed. The residue was purified on a flash chromatography column with EtOAc/hexanes to afford 4-(4-nitrophenyl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (3.66 g, 78% yield) as a white solid. ES-MS for C16H23N3O4 calcd. (m/e) 321, observed 322 (M+H).

Workup

customThis compound was prepared in a similar way
washwashed with water (100 mL), brine (50 mL)
dry with materialdried with anhydrous sodium sulfate
customthe solvent was removed
customThe residue was purified on a flash chromatography column with EtOAc/hexanes

Sources & evidence

ORD record: ord-9b92f0d1417e4fbcbf4974b1c30fdb85
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211884B2

Reaction notes

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