1,5-Dibromopentane → HCID 19734240, compound

HRID 327082Notes

Reaction equation

HRID 327082 reaction equation
O.[NH2:2][CH2:3][CH:4]1[C:10]2=[CH:11][NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[C:8]([C:9]=32)[C:7](=[O:17])[NH:6][CH2:5]1.C(N(CC)CC)C.Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]Br>CN(C)C=O>[N:2]1([CH2:3][CH:4]2[C:10]3=[CH:11][NH:12][C:13]4[CH:14]=[CH:15][CH:16]=[C:8]([C:9]=43)[C:7](=[O:17])[NH:6][CH2:5]2)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 8471TriethylamineHCID 19734268HCID 19734268, compound

Product 1

HCID 19734240HCID 19734240, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4 g of 3-aminomethyl-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-Cd]indole hydrate (for preparation see Example 1C) were dissolved in 40 ml of dimethylformamide. 2.6 ml of triethylamine were added to the solution and subsequently, while stirring at room temperature, 2 4 ml of 1,5-dibromopentane were added. The reaction mixture was heated at 50° C. for 3.5 hours. The reaction mixture was worked up by evaporating it under reduced pressure (water pump vacuum) and taking up the residue in a 9:1 dichloromethane/methanol mixture. Then saturated aqueous sodium carbonate solution was added until pH 11 was reached. The organic phase was separated and the aqueous phase was washed twice more with 50 ml portions of the dichloromethane/methanol mixture. The combined organic phases were dried over sodium sulfate, filtered and evaporated. The residue was dissolved in ethanol, and diethyl ether was added to the solution until a slight turbidity appeared. The resulting crystals were filtered out and dried. 3.5 g of crystalline 3-(1-piperidinylmethyl)-3,4,5,6-tetrahydro-6-oxo-1H-azepino[5,4,3-cd]indole were obtained with a melting point of 119° to 122° C.

Workup

  1. temperatureThe reaction mixture was heated at 50° C. for 3.5 hours
  2. customby evaporating it under reduced pressure (water pump vacuum)
  3. additionThen saturated aqueous sodium carbonate solution was added until pH 11
  4. customThe organic phase was separated
  5. washthe aqueous phase was washed twice more with 50 ml portions of the dichloromethane/methanol mixture
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. dissolutionThe residue was dissolved in ethanol
  10. additiondiethyl ether was added to the solution until a slight turbidity
  11. filtrationThe resulting crystals were filtered out
  12. customdried

Sources & evidence

ORD record
ord-a4b8439bdcd04e7da7ce7cacb0fcf2d3
Source dataset
uspto-grants-1993_12
Patent number
US05272143

Reaction notes

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