Potassium Carbonate → HCID 60069826, compound

HRID 549267Notes

Reaction equation

HRID 549267 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2Cl)=[CH:4][CH:3]=1.[C:13]([N:20]1[CH2:26][CH2:25]C[NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[C:9]2[N:23]2[CH2:22][CH2:21][N:20]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:26][CH2:25]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 65020247-Bromo-1-Chloroisoquinoline

Product 1

HCID 60069826HCID 60069826, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 7-bromo-1-chloroisoquinoline (3.14 g, 13 mmol) in DMSO (20 mL) at room temperature was added either carboxylic acid tert-butyl (BOC)piperazine (7.23 g, 38.8 mmol) or BOC-homopiperazine (7.77 g, 38.8 mmol) and then potassium carbonate (5.36 g, 39 mmol). The mixture was heated to 110° C. for 24 h. On cooling, the mixture was poured onto ice/water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic phases were washed with water 50 mL) and brine (50 mL). Before drying over anhydrous sodium sulfate. Removal of solvent under reduced pressure gave crude product. Purification was performed by applying the crude material to a plug of silica in a filter funnel and eluting with heptane/ethyl acetate (2:1) and gave 2.73 g (54%) yellow oil. 1H NMR (CDCl3) δ 8.20-8.22 (m, 1H), 8.13-8.18 (d, J=6 Hz, 1H), 7.65-7-71 (dd, J=12, 3 Hz, 1H), 7.59-7.65 (d, J=12 Hz, 1H), 7.21-7.25 (m, 1H), 3.64-3.73 (m, 4H), 7.27-7.36 (m, 4H), 1.49 (s, 9H); LCMS: 392, 394, 395.

Workup

  1. temperatureOn cooling
  2. additionthe mixture was poured onto ice/water (50 mL)
  3. extractionextracted with ethyl acetate (3×50 mL)
  4. washThe combined organic phases were washed with water 50 mL) and brine (50 mL)
  5. dry with materialBefore drying over anhydrous sodium sulfate
  6. customRemoval of solvent under reduced pressure
  7. customgave crude product
  8. customPurification
  9. washeluting with heptane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-32ce83c4efa44273b273320447a41211
Source dataset
uspto-grants-2011_05
Patent number
US07943639B2

Reaction notes

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