Ethyl Bromide → HCID 9813187, compound

HRID 1582445Notes

Reaction equation

HRID 1582445 reaction equation
[CH2:1]1[C:7]2=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4][NH:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:22][CH3:23]>C(#N)C>[CH2:22]([N:3]1[CH2:2][CH2:1][C:7]2=[CH:8][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=3[N:6]2[CH2:5][CH2:4]1)[CH3:23]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 97940922,3,4,5-Tetrahydro-1H-[1,4]diazepino[1,7-a]indole

Product 1

HCID 9813187HCID 9813187, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole (280 mg, 1.5 mmol) in acetonitrile (15 mL) is treated with powdered potassium carbonate (622 mg, 4.5 mmol) and bromoethane (0.12 mL, 1.65 mmol, filtered through a pad of celite). The resulting milky suspenesion is heated to 40° C. After 22 hrs, the volatiles are removed under reduced pressure, diluted with water (20 mL), and extracted twice with ethyl acetate (20 mL). The combined organics are washed with brine (20 mL), dried over MgSO4, filtered, and concentrated to give a crude oil. This material is purified by LC (230-400 silica gel) eluting with 5% methanol/dichloromethane to afford 226 mg of 3-ethyl-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole as a white solid, mp 44-46° C. IR (drift) 2931, 2808, 1466, 1413, 1373, 1348, 1323, 1315, 1243, 1132, 1104, 776, 749, 732, 688 cm−1.

Workup

  1. filtrationfiltered through a pad of celite)
  2. customthe volatiles are removed under reduced pressure
  3. additiondiluted with water (20 mL)
  4. extractionextracted twice with ethyl acetate (20 mL)
  5. washThe combined organics are washed with brine (20 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a crude oil
  10. customThis material is purified by LC (230-400 silica gel)
  11. washeluting with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-61d0127933da4ded971472a2020504ec
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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