1-Bromo-2,6-dichlorobenzene → HCID 57979791, compound

HRID 1868113Notes

Reaction equation

HRID 1868113 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1Br.[C:10]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:13]([O:12][C:10]([N:17]1[CH2:22][CH2:21][N:20]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[CH2:19][CH2:18]1)=[O:11])([CH3:16])([CH3:14])[CH3:15]

Participants

6

Reactant 4

HCID 295681-Bromo-2,6-dichlorobenzeneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxide

Product 1

HCID 57979791HCID 57979791, compound

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
110 °C

Procedure

2,6-dichlorobromobenzene (2.26 g, 10 mmole), N-Boc-piperazine (2.05 g, 11 mmole), Pd2(dba)3 (92 mg, 1 mol %), BINAP (187 mg, 3 mol %), and sodium tert-butoxide (1.15 g, 12 mmole) were charged in a microwave vessel. The vessel was capped, purged with nitrogen, and 20 mL toluene added. The reaction mixture was heated to 110° C. for 30 minutes in the microwave and then the mixture was filtered through celite, rinsing with EtOAc. The filtrate was evaporated and then filtered through a pad of silica gel, eluting with dichloromethane. Evaporation gave crude 4-(2,6-Dichloro-phenyl)-piperazine-1-carboxylic acid tert-butyl ester as an orange oil that was taken on to the next step without further purification.

Workup

  1. customThe vessel was capped
  2. custompurged with nitrogen, and 20 mL toluene
  3. additionadded
  4. filtrationthe mixture was filtered through celite
  5. washrinsing with EtOAc
  6. customThe filtrate was evaporated
  7. filtrationfiltered through a pad of silica gel
  8. washeluting with dichloromethane
  9. customEvaporation

Sources & evidence

ORD record
ord-97615c39980b40a4833b9bc33937be31
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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