Aluminium lithium hydride → HCID 22896288, compound

HRID 1017196Notes

Reaction equation

HRID 1017196 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([C:15]=2[C:16]([C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][NH: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][C@H:18]2[CH2:23][CH2:22][CH2:21][CH2:20][NH: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 22896286HCID 22896286, compound

Product 1

HCID 22896288HCID 22896288, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 2.4 g (7.9 mmol) of (2-phenyl-1H-indol-3-yl)piperidin-2(R)-ylmethanone in anhydrous tetrahydrofuran (15 ml) under an atmosphere of nitrogen was added cautiously over 5 min a solution of lithium aluminium hydride (12.5 ml of a 1M solution in tetrahydrofuran, 12.5 mmol) at 0° C. The mixture was heated under reflux for 13 hr, after which it was cooled and quenched by careful addition of water (0.5 ml), 4N NaOH (0.5 ml), and water (1.5 ml). The mixture was stirred for 10 min then filtered through hyflo and evaporated in vacuo to afford 1.2 g (4.1 mmol; 52%) of 2-phenyl-3-(piperidin-2(R)-ylmethyl)-1H-indole as a yellow oil. δH (360 MHz; CDCl3) 1.09-1.26 (1H, m, aliphatic), 1.38-1.52 (1H, m, aliphatic), 1.60-1.74 (3H, m, aliphatics), 1.74-1.90 (1H, m, aliphatic), 2.67-2.80 (1H, m, aliphatic), 3.12-3.25 (1H, m, aliphatic), 3.28-3.38 (2H, m, aliphatics), 3.69 (1H, dd, J 13.8 and 4.2, indole CHAHB), 7.06-7.21 (2H, m, aromatics), 7.29-7.49 (4H, m, aromatics), 7.58 (1H, d, J 7.2, aromatics), 7.81 (1H, d, J 7.6, aromatic), 9.15 (1H, br s, NH); m/z (ES+) 291 (M++H, 100%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 13 hr
  3. temperatureafter which it was cooled
  4. customquenched by careful addition of water (0.5 ml), 4N NaOH (0.5 ml), and water (1.5 ml)
  5. filtrationthen filtered through hyflo
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-fc3bdeebac5a4cb7bfc360e53922c2e4
Source dataset
uspto-grants-2002_11
Patent number
US06479480B1

Reaction notes

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