Dimethylformamide → Isobutyl 1-(3-chloroisoquinolin-1-yl)piperidin-4-ylcarbamate

HRID 2245233Notes

Reaction equation

HRID 2245233 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([Cl:12])[N:3]=1.[NH:13]1[CH2:18][CH2:17][CH:16]([NH:19][C:20](=[O:26])[O:21][CH2:22][CH:23]([CH3:25])[CH3:24])[CH2:15][CH2:14]1.CCN(CC)CC.CN(C=O)C>O>[Cl:12][C:4]1[N:3]=[C:2]([N:13]2[CH2:14][CH2:15][CH:16]([NH:19][C:20](=[O:26])[O:21][CH2:22][CH:23]([CH3:24])[CH3:25])[CH2:17][CH2:18]2)[C:11]2[C:6]([CH:5]=1)=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 2986251,3-DichloroisoquinolineHCID 15676964HCID 15676964, compound

Product 1

HCID 59216558Isobutyl 1-(3-chloroisoquinolin-1-yl)piperidin-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1,3-dichloroisoquinoline (0.16 g, 0.78 mmol), isobutyl piperidin-4-ylcarbamate (0.16 g, 0.78 mmol), Et3N (0.11 mL, 0.78 mmol), and DMF (0.5 mL) was sealed in a microwave vessel and heated by microwave irradiation at 160° C. for three minutes. The reaction was cooled to room temperature, diluted with water, and extracted with CH2Cl2. The combined extracts were washed with water, dried over Na2SO4, and concentrated under reduced pressure to yield isobutyl 1-(3-chloroisoquinolin-1-yl)piperidin-4-ylcarbamate. LC/MS: m/z 362.2 (M+H)+ at 3.98 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customwas sealed in a microwave vessel
  2. temperatureThe reaction was cooled to room temperature
  3. extractionextracted with CH2Cl2
  4. washThe combined extracts were washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-abb0c9b9cf6945f895b07e78ffd1088c
Source dataset
uspto-grants-2010_03
Patent number
US07683066B2

Reaction notes

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