Hydrochloric Acid → 6-(1,4-Diazepan-1-yl)-1-(4,4,4-trifluorobutyl)-benzo[cd]indol-2(1H)-one

HRID 433098Notes

Reaction equation

HRID 433098 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9]3[C:10](=[CH:16][CH:17]=[CH:18][C:8]=3[C:7]1=[O:19])[C:11](Br)=[CH:12][CH:13]=2.[NH:22]1[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1.CC(C)([O-])C.[Na+].Cl>O.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].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.C1(C)C=CC=CC=1>[N:22]1([C:11]2[C:10]3[C:9]4[C:14](=[CH:13][CH:12]=2)[N:6]([CH2:5][CH2:4][CH2:3][C:2]([F:21])([F:20])[F:1])[C:7](=[O:19])[C:8]=4[CH:18]=[CH:17][CH:16]=3)[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 68163Hexahydro-1,4-diazepineHCID 187579401-(4,4,4-Trifluorobutyl)-6-bromo-benzo[cd]indol-2(1h)-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 121138336-(1,4-Diazepan-1-yl)-1-(4,4,4-trifluorobutyl)-benzo[cd]indol-2(1H)-oneYield 108.5%

Reagents, catalysts & solvents 4

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 1-(4,4,4-trifluorobutyl)-6-bromo-benzo[cd]indol-2(1H)-one (1.225 g, 3.42 mmol), homopiperazine (6 g, 60 mmol) and toluene (100 ml) in a round bottomed flask was added BINAP (42 mg, 2%) and Pd2(dba)3 (30 mg, 1%) and sodium tert-butoxide (333 mg, 3.46 mmol). The reaction mixture was heated at 85° C. for 18 hours and was then poured into 500 ml concentrated HCl solution in water. The organic layer was seperated and the aqueous layer was extracted with more toluene (2×500 ml). The combined organic layers were neutralized with 10 N NaOH (aqueous ) and extracted with a one to one mixture of dichloromethane and toluene (3×500 ml). The combined organic layers were dried and filtered and concentrated to give the crude product (1.4 g).

Workup

  1. customThe organic layer was seperated
  2. extractionthe aqueous layer was extracted with more toluene (2×500 ml)
  3. extractionextracted with a one to one mixture of dichloromethane and toluene (3×500 ml)
  4. customThe combined organic layers were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-31ad57b91b62496abb888d1c79fabff2
Source dataset
uspto-grants-2003_12
Patent number
US06667303B1

Reaction notes

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