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

HRID 1005654Notes

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 5-fluoro-2-nitrotoluene (2 mL, 16.4 mmol), 1-tert-butoxycarbonyl piperazine (3.35 g, 18 mmol) and potassium carbonate (2.76 g, 20 mmol) in 7 mL of DMSO was stirred and heated at 100° C. for 2 h. Water (40 mL) and hexane (30 mL) were added and the bright yellow precipitate was collected, washed with water and hexane, and dried in vacuo to afford 4.9 g of 4-(3-methyl-4-nitrophenyl)-piperazine-1-carboxylic acid tert-butyl ester, m.p. 145-146° C.

Workup

customthe bright yellow precipitate was collected
washwashed with water and hexane
customdried in vacuo

Sources & evidence

ORD record: ord-e6e1f22f6b5c49c98197df727bb5073f
Source dataset: uspto-grants-2004_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06787535B2

Reaction notes

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