Aluminium lithium hydride → HCID 22397012, compound

HRID 1356254Notes

Reaction equation

HRID 1356254 reaction equation
[NH:1]([C:8](=O)[CH2:9][N:10]1[C:18]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:12]2[CH2:19][CH2:20][N:21](C(OC(C)(C)C)=O)[CH2:22][CH2:23][C:11]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:19]1[C:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[N:10]([CH2:9][CH2:8][NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:11]=2[CH2:23][CH2:22][NH:21][CH2:20]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22396890HCID 22396890, compound

Product 1

HCID 22397012HCID 22397012, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 6-(2-anilino-2-oxoethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.059 g, 0.14 mmol) was dissolved in THF (5 mL) and LAH (0.0080 g, 0.21 mmol, 1.5 equiv.) was added. The reaction mixture was refluxed for 6 h under N2. The reaction mixture was quenched with water and extracted with EtOAc. The extracts were treated with TFA, and the resulting mixture was concentrated. THF and excess LAH were added and the reaction mixture was refluxed for 2 h. The reaction mixture was quenched by the addition of acetone, methanol, and water. The resulting mixture was extracted with EtOAc (4×) and the reaction mixture was concentrated. The crude product was purified by PTLC (1 mm×20 cm×20 cm plate, developed with 10% MeOH:CH2Cl2, eluted with MeOH) to yield N-[2-(2,3,4,5-tetrahydroazepino[4,5-b]indol-6(1H)-yl)ethyl]aniline (0.0093 g) in 22% yield. 1H NMR (400 MHz, CDCl3) δ 2.87-2.89, 2.93-2.96, 3.03, 3.09, 3.49-3.53, 4.31, 6.57, 6.74, 7.07-7.28, 7.50.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h under N2
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with EtOAc
  4. additionThe extracts were treated with TFA
  5. concentrationthe resulting mixture was concentrated
  6. additionTHF and excess LAH were added
  7. temperaturethe reaction mixture was refluxed for 2 h
  8. customThe reaction mixture was quenched by the addition of acetone, methanol, and water
  9. extractionThe resulting mixture was extracted with EtOAc (4×)
  10. concentrationthe reaction mixture was concentrated
  11. customThe crude product was purified by PTLC (1 mm×20 cm×20 cm plate, developed with 10% MeOH:CH2Cl2, eluted with MeOH)

Sources & evidence

ORD record
ord-224283c99fe4484d8a69c3aff0493cb8
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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