HCID 9834916, compound → HCID 9920993, compound

HRID 1582448Notes

Reaction equation

HRID 1582448 reaction equation
[N+:1](/[CH:4]=[CH:5]/[C:6]1[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:8]2[CH2:15][CH2:16][NH:17][CH2:18][CH2:19][C:7]=12)([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:19]1[C:7]2=[C:6]([CH2:5][CH2:4][NH2:1])[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[N:8]2[CH2:15][CH2:16][NH:17][CH2:18]1

Participants

4

Reactant 2

HCID 9834916HCID 9834916, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 9920993HCID 9920993, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 11-[(E)-2-nitroethenyl]-2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole (236 mg, 0.92 mmol) in THF (9 mL) is cooled to 0° C. and treated with lithium aluminum hydride (1M THF, 2.8 mL, 2.8 mmol) with gas evolution. The reaction is heated to reflux for 4 hrs followed by cooling to rt for 16 hrs. At this time, the reaction mixture is quenched by the successive addition of 0.11 mL water, 0.10 mL 5N NaOH, and 0.37 mL water. The resulting thick gelatinous suspension is diluted with dichloromethane (30 mL), filtered through celite, and concentrated to give a crude oil. This material is purified by LC (230-400 silica gel) eluting with 20:2.5:77.5 methanol/ammonuim hydroxide/dichloromethane to afford 92 mg of 2-(2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indol-11-yl)-1-ethanamine as a yellow syrup. IR (liq.) 3353, 3307, 3087, 3048, 3025, 2935, 2844, 1469, 1426, 1373, 1340, 1324, 1181, 1015, 742 cm−1; MS (FAB) m/z 230 (MH+).

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 4 hrs
  3. customAt this time, the reaction mixture is quenched by the successive addition of 0.11 mL water, 0.10 mL 5N NaOH, and 0.37 mL water
  4. additionThe resulting thick gelatinous suspension is diluted with dichloromethane (30 mL)
  5. filtrationfiltered through celite
  6. concentrationconcentrated
  7. customto give a crude oil
  8. customThis material is purified by LC (230-400 silica gel)
  9. washeluting with 20:2.5:77.5 methanol/ammonuim hydroxide/dichloromethane

Sources & evidence

ORD record
ord-c7210bad7b4d4a58ad9344ded3cc8a6a
Source dataset
uspto-grants-2004_05
Patent number
US06734301B2

Reaction notes

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