Dimethylformamide → Tert-butyl 4-(3-methyl-4-nitrophenyl)piperazine-1-carboxylate

HRID 415063Notes

Reaction equation

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

Participants

Conditions

Temperature: 50 °C

Procedure

5-Fluoro-2-nitrotoluene (1 mL, 8.20 mmol, commercially available from Aldrich), Boc-piperazine (1.68 g, 9.02 mmol, commercially available from Aldrich), anhydrous potassium carbonate (2.27 g, 16.40 mmol) and DMF (25 mL) were combined and heated to 50° C. for 24 hours. Upon allowing the reaction mixture to cool to room temperature, water was added to the reaction mixture and the resulting precipitate was filtered as product, washed with ether and dried under reduced pressure to give 2.21 g tert-butyl 4-(3-methyl-4-nitrophenyl)piperazine-1-carboxylate. 1H-NMR (400 MHz, CDCl3), δ 7.96 (d, 1H), 6.90 (s, 1H), 6.85 (s, 1H), 3.35 (m, 4H), 3.19 (m, 4H), 2.55 (s, 3H), 1.42 (s, 9H). MS (EI): 322 (MH+).

Workup

temperatureto cool to room temperature
filtrationthe resulting precipitate was filtered as product
washwashed with ether
customdried under reduced pressure

Sources & evidence

ORD record: ord-04075e77651049dd9457994d6fd4ffaa
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08088767B2

Reaction notes

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