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Potassium Carbonate → 1-chloro-4-(octahydroisoquinolin-2(1H)-yl)phthalazine

HRID 503533
Notes
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Reaction equation

HRID 503533 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([Cl:12])=[N:4][N:3]=1.[CH2:13]1[CH:22]2[CH:17]([CH2:18][CH2:19][CH2:20][CH2:21]2)[CH2:16][CH2:15][NH:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O>[Cl:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([N:14]2[CH2:15][CH2:16][CH:17]3[CH:22]([CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:13]2)=[N:3][N:4]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 784901,4-DichlorophthalazineHCID 97812Decahydroisoquinoline

Product 1

HCID 594273491-chloro-4-(octahydroisoquinolin-2(1H)-yl)phthalazine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
80 °C

Procedure

A resealable pressure bottle was charged with 1,4-dichlorophthalazine (1258 mg, 6.28 mmol), decahydroisoquinoline (588 μl, 3.95 mmol), potassium carbonate (546 mg, 3.95 mmol) and DMSO (20 mL, 0.2 M). Reaction was stirred at 80° C. for 16 h, then cooled to RT and diluted with 5 mL of DMSO. The solution was purified by Gilson HPLC (10% to 90% CH3CN/H2O/0.1% TFA) to afford 1-chloro-4-(octahydroisoquinolin-2(1H)-yl)phthalazine. MS [M+H]=302.1. Calcd for C17H20ClN3: 301.8.

Workup

  1. customReaction
  2. temperaturecooled to RT
  3. customThe solution was purified by Gilson HPLC (10% to 90% CH3CN/H2O/0.1% TFA)

Sources & evidence

ORD record
ord-1784cd7983a2447cb36bf11ac820341b
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07776857B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes