Water → HCID 18377395, compound

HRID 2301137Notes

Reaction equation

HRID 2301137 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C.Br[CH2:26][CH2:27][CH2:28][CH2:29][C:30]12[CH2:41][CH2:40][CH2:39][C:37]3[C:38]1=[C:33]([CH:34]=[CH:35][CH:36]=3)[NH:32][C:31]2=[O:42].C(=O)([O-])[O-].[K+].[K+].O>CO.Cl.CN(C)C=O>[CH:24]1[C:19]2[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([N:11]3[CH2:10][CH2:9][N:8]([CH2:26][CH2:27][CH2:28][CH2:29][C:30]45[CH2:41][CH2:40][CH2:39][C:37]6[C:38]4=[C:33]([CH:34]=[CH:35][CH:36]=6)[NH:32][C:31]5=[O:42])[CH2:13][CH2:12]3)[C:20]=2[CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 105908942a-(4-Bromobutyl)-2a,3,4,5-tetrahydrobenz[cd]indole-2(1H)-oneHCID 18377378HCID 18377378, compound

Product 1

HCID 18377395HCID 18377395, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21893726Hydrochloride methanolSolvent

Conditions

Temperature
40 °C

Procedure

1-t-Butoxycarbonyl-4-(6,7,8,9-tetrahydro-5H-benzocyclohepten-5-yl)piperazine (340 mg, 1.0 mmol) was dissolved in 10% hydrochloric acid methanol (4 ml) and stirred at 40° C. for 3.5 hours. The solvent was removed by evaporation under a reduced pressure, and the thus obtained residue was mixed with 2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (310 mg, 1.0 mmol) and potassium carbonate (490 mg, 3.5 mmol) and stirred overnight at room temperature in N,N-dimethylformamide (3 ml). This was mixed with water, the precipitate was collected by filtration and then the reaction product was extracted from the mother liquid with ethyl acetate. The extract was washed with water and saturated brine and dried with anhydrous sodium hydrogensulfate, the solvent was removed by evaporation under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography. The thus purified compound was combined with the aforementioned precipitate and thoroughly washed with ethyl acetate to obtain 370 mg (0.81 mmol, 80%) of the title compound.

Workup

  1. customThe solvent was removed by evaporation under a reduced pressure
  2. filtrationthe precipitate was collected by filtration
  3. extractionthe reaction product was extracted from the mother liquid with ethyl acetate
  4. washThe extract was washed with water and saturated brine
  5. dry with materialdried with anhydrous sodium hydrogensulfate
  6. customthe solvent was removed by evaporation under a reduced pressure
  7. customthe thus obtained material was separated
  8. custompurified by a silica gel column chromatography
  9. washthoroughly washed with ethyl acetate

Sources & evidence

ORD record
ord-ce005f95961d4fa2a097add33f75a77d
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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