1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-Butyl 4-(isoquinolin-1-yl)piperazine-1-carboxylate

HRID 241340Notes

Reaction equation

HRID 241340 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=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].C1CCN2C(=NCCC2)CC1>O>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 140539Isoquinoline, 1-chloro-HCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 54451864tert-Butyl 4-(isoquinolin-1-yl)piperazine-1-carboxylateYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
107.5 °C

Procedure

1-Chloro-isoquinoline (176 mg, 1.07 mmol), piperazine-1-carboxylic acid tert-butyl ester (420 mg, 2.26 mmol) and DBU (0.25 mL, 1.61 mmol) were added into DMP (2 mL). The mixture was heated to 105-110° C. for overnight. The residue was diluted with water and extracted with ether. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo to dryness. The resulting residue was purified by column chromatography (5% to 10% ethyl acetate/hexane) to give 222 mg of the desired product 4-isoquinolin-1-yl-piperazine-1-carboxylic acid tert-butyl ester (yield: 66%).

Workup

  1. extractionextracted with ether
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo to dryness
  5. customThe resulting residue was purified by column chromatography (5% to 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-8e78db9b8faa4d89a00c86d51a570f21
Source dataset
uspto-grants-2014_02
Patent number
US08648197B2

Reaction notes

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