N,N-Dimethyl-1,3-propanediamine → 5-bromo-N-(3-(dimethylamino)propyl)isoquinolin-1-amine

HRID 908313Notes

Reaction equation

HRID 908313 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2Cl.[CH3:13][N:14]([CH2:16][CH2:17][CH2:18][NH2:19])[CH3:15]>N1C=CC=CC=1.C(Cl)Cl.O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[C:7]2[NH:19][CH2:18][CH2:17][CH2:16][N:14]([CH3:15])[CH3:13]

Participants

6

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 211924975-Bromo-1-chloroisoquinoline

Product 1

HCID 673868285-bromo-N-(3-(dimethylamino)propyl)isoquinolin-1-amineYield 25%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a microwave vial containing 5-bromo-1-chloroisoquinoline (Step 3, 0.300 g, 1.2 mmol), dissolved in pyridine (3 mL), was added Dimethylaminopropyl-amine (0.16 mL, 1.3 mmol). The mixture was placed into CEM Microwave for 8 minutes at 100° C., while supplying 80 Watts of power via power-max. The mixture was diluted with DCM and water, and extracted with DCM (3×10 mL). Then dried organics (over sodium sulfate) was filtered, and concentrated in-vacuo. It was then purified by Amino-Propyl Silica-gel chromatography in MeOH/DCM. This gave tan colored oil, which was titled product (0.085 g, 0.3 mmol). MS (ESI pos. ion) m/z: 309; 310 (M+H). Calc'd Exact Mass for C14H18N3Br: 308

Workup

  1. extractionextracted with DCM (3×10 mL)
  2. filtrationThen dried organics (over sodium sulfate) was filtered
  3. concentrationconcentrated in-vacuo
  4. customIt was then purified by Amino-Propyl Silica-gel chromatography in MeOH/DCM

Sources & evidence

ORD record
ord-f5e6dd56f0594a518598c5d20720a23f
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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