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p-Fluoronitrobenzene → 1-Methyl-4-(4-nitrophenyl)-1,4-diazepane

HRID 987507
Notes
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Reaction equation

HRID 987507 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[CH3:11][N:12]1[CH2:18][CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(Cl)Cl>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([N:15]2[CH2:16][CH2:17][CH2:18][N:12]([CH3:11])[CH2:13][CH2:14]2)=[CH:3][CH:4]=1)([O-:10])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 10796Cesium carbonateHCID 2283491-Methylhomopiperazine

Product 1

HCID 31247221-Methyl-4-(4-nitrophenyl)-1,4-diazepane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344Dichloromethane
Solvent

Conditions

Temperature
100 °C

Procedure

The mixture of 1 -fluoro-4-nitrobenzene (880 mg, 6.2 mmol), 1-methylhomopiperazine (2.3 mL, 18.6 mmol), Cs2CO3 (6.1 g, 18.6 mmol) in 20 mL DMF was stirred at 100° C. for 1.5 hr. It was diluted with DCM, filtered to remove the inorganic salts, washed with water, dried, evaporated in vacuuo to afford 1-(4-nitrophenyl)-4-methylhomopiperazine in quantitative yield. ES-MS: (M+H)+236.

Workup

  1. filtrationfiltered
  2. customto remove the inorganic salts
  3. washwashed with water
  4. customdried
  5. customevaporated in vacuuo

Sources & evidence

ORD record
ord-477b6a04ce3c4bb1b3299c5aaabbffd5
Source dataset
uspto-grants-2003_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06632815B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes