1,5-Dibromopentane → Ethyl 8,9-dimethoxy-3-methyl-2-(3-piperidinyl-phenyl)-5,6-dihydro-pyrrolo[2,1-a]-isoquinoline-1-carboxylate

HRID 585080Notes

Reaction equation

HRID 585080 reaction equation
[CH2:1]1[CH2:11][CH2:10]N2C(=NCCC2)[CH2:3][CH2:2]1.BrCCCCCBr.[NH2:19][C:20]1[CH:21]=[C:22]([C:26]2[C:27]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[C:28]3[C:37]4[C:32](=[CH:33][C:34]([O:40][CH3:41])=[C:35]([O:38][CH3:39])[CH:36]=4)[CH2:31][CH2:30][N:29]3[C:42]=2[CH3:43])[CH:23]=[CH:24][CH:25]=1>CN(C=O)C>[CH3:41][O:40][C:34]1[CH:33]=[C:32]2[C:37](=[CH:36][C:35]=1[O:38][CH3:39])[C:28]1=[C:27]([C:44]([O:46][CH2:47][CH3:48])=[O:45])[C:26]([C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([N:19]4[CH2:10][CH2:11][CH2:1][CH2:2][CH2:3]4)[CH:21]=3)=[C:42]([CH3:43])[N:29]1[CH2:30][CH2:31]2

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10179495Ethyl 2-(3-aminophenyl)-8,9-dimethoxy-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate

Product 1

HCID 10227320Ethyl 8,9-dimethoxy-3-methyl-2-(3-piperidinyl-phenyl)-5,6-dihydro-pyrrolo[2,1-a]-isoquinoline-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

168.5 mg (1.11 mmol) of DBU and 84.9 mg (0.37 mmol) of 1,5-dibromopentane were added to a solution of 150 mg (0.37 mmol) of ethyl 2-(3-aminophenyl)-8,9-dimethoxy-3-methyl-5,6-dihydropyrrolo[2,1-a]isoquinoline-1-carboxylate (Example 28) in 3 mL of DMF. The mixture was stirred at 120° C. for 20 hours, then evaporated under reduced pressure, and the residue was taken up in an ethyl acetate/water mixture. The layers were separated, the aqueous layer was extracted with ethyl acetate, and the combined organic phases were washed with water, dried over Na2SO4, and the solvent was evaporated under reduced pressure. Chromatography on a short silica gel column using a dichloromethane/ethyl acetate 10:1 mixture as eluant, followed by crystallization from diethyl ether gave the title compound.

Workup

  1. customevaporated under reduced pressure
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic phases were washed with water
  5. dry with materialdried over Na2SO4
  6. customthe solvent was evaporated under reduced pressure
  7. customfollowed by crystallization from diethyl ether

Sources & evidence

ORD record
ord-0246abcbbc7649d8aa3ea9145c71d2ce
Source dataset
uspto-grants-2005_08
Patent number
US06930114B2

Reaction notes

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