Aluminium lithium hydride → 4-[4-(6-Methyl-thieno[2,3-d]isoxazol-3-yl)-piperidin-1-yl]-butylamine

HRID 1986917Notes

Reaction equation

HRID 1986917 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1[C:15]2[O:14][N:13]=[C:12]([CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][C:25]#[N:26])[CH2:18][CH2:17]3)[C:11]=2[S:10][CH:9]=1>O1CCCC1>[CH3:7][C:8]1[C:15]2[O:14][N:13]=[C:12]([CH:16]3[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH2:18][CH2:17]3)[C:11]=2[S:10][CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 231368314-[4-(6-Methylthieno[2,3-d]isoxazol-3-yl)-piperidin-1-yl]-butyronitrile

Product 1

HCID 231368174-[4-(6-Methyl-thieno[2,3-d]isoxazol-3-yl)-piperidin-1-yl]-butylamineYield 68.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under inert conditions, add lithium aluminum hydride (3.42 mmol, 3.42 mL, 1.50 equivalents, 1.0 M solution in tetrahydrofuran) to a stirred solution of 4-[4-(6-methyl-thieno[2,3-d]isoxazol-3-yl)-piperidin-1-yl]-butyronitrile (2.28 mmol, 660 mg, 1.00 equivalents) in tetrahydrofuran (dry, 12.86 mL). Stir the resulting solution at room temperature for 2.5 hours. Quench the reaction mixture by adding water (0.16 mL), then sodium hydroxide (aqueous, 0.16 mL, 2 M solution), and then water (0.5 mL). Dilute the resulting suspension with dichloromethane (16 mL) and vigorously stir for 30 minutes. Filter the resulting mixture through a bed of celite®, dry over magnesium sulfate, filter and evaporate to yield the desired product (457 mg) as a brown oil. LC/MS (ESI), m/e 294 (MH+), retention time 0.56 minutes. Condition II.

Workup

  1. customQuench the reaction mixture
  2. additionby adding water (0.16 mL)
  3. additionDilute the resulting suspension with dichloromethane (16 mL)
  4. stirringvigorously stir for 30 minutes
  5. filtrationFilter the resulting mixture through a bed of celite®
  6. dry with materialdry over magnesium sulfate
  7. filtrationfilter
  8. customevaporate

Sources & evidence

ORD record
ord-7c97411f7d654ecc9c060366c06719b7
Source dataset
uspto-grants-2009_06
Patent number
US07550469B2

Reaction notes

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