Aluminium lithium hydride → HCID 18403270, compound

HRID 1017195Notes

Reaction equation

HRID 1017195 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:16]([CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=O)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[CH2:16][CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54425483HCID 54425483, compound

Product 1

HCID 18403270HCID 18403270, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 7.5 g (24.7 mmol) of (2-phenyl-1H-indol-3-yl)piperidin-3-ylmethanone in anhydrous tetrahydrofuran (100 ml) under an atmosphere of nitrogen was added cautiously over 5 min a solution of lithium aluminium hydride (50 ml of a 1M solution in tetrahydrofuran, 50 mmol) at 0° C. The mixture was heated at reflux for 3 hr, after which it was cooled and quenched by the careful addition of water (2 ml), 4N NaOH (2 ml), and water (6 ml). The mixture was stirred for 10 min then filtered through hyflo and evaporated in vacuo to afford 5.6 g (19.3 mmol; 78%) of 2-phenyl-3-(piperidin-3-ylmethyl)-1H-indole as a clear oil. δH (360 MHz; CDCl3) 1.00-1.13 (1H, m, aliphatic), 1.28-1.40 (1H, m, aliphatic), 1.44-1.62 (2H, m, aliphatics), 1.74-1.86 (1H, m, aliphatic), 2.27 (1H, t, J 10.3, aliphatic), 2.44-2.52 (1H, m, aliphatic), 2.75 (2H, dd, J 7.2 and 3.3, aliphatics), 2.91-3.03 (2H, m, aliphatics), 7.12 (1H, t, J 7.9 and 7.1, indole H5), 7.19 (1H, t, J 7.9 and 7.0, indole H6), 7.32-7.39 (2H, m, aromatics), 7.42-7.50 (2H, m, aromatics), 7.54 (2H, dd, J 8.5 and 1.4, aromatics), 7.62 (1H, d, J 7.1, indole H4), 8.10 (1H, br s, NH); m/z (ES+) 291 (M++H, 100%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3 hr
  3. temperatureafter which it was cooled
  4. customquenched by the careful addition of water (2 ml), 4N NaOH (2 ml), and water (6 ml)
  5. filtrationthen filtered through hyflo
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-26c00647d37448bf8ed924a40274eb70
Source dataset
uspto-grants-2002_11
Patent number
US06479480B1

Reaction notes

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