Water → 4-(2-(azepan-1-yl)ethyl)-4,5,6,7-tetrahydro-1-phenyl-1H-indazole

HRID 1943616Notes

Reaction equation

HRID 1943616 reaction equation
[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][CH2:12][CH:11]([CH2:16][C:17]([N:19]4[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]4)=O)[C:10]=3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[N:19]1([CH2:17][CH2:16][CH:11]2[CH2:12][CH2:13][CH2:14][C:15]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[N:8]=[CH:9][C:10]2=3)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59553057HCID 59553057, compound

Product 1

HCID 115588474-(2-(azepan-1-yl)ethyl)-4,5,6,7-tetrahydro-1-phenyl-1H-indazoleYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 1-(2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)acetyl)azepane (60 mg, 0.18 mmol) in anhydrous THF (2 mL) is slowly added to a suspension of LiAlH4 (20 mg, 0.53 mmol) in anhydrous THF (10 mL) cooled to 0° C. The mixture is refluxed for 3 hours following the reaction by means of TLC. The mixture is cooled, and water and a NaOH solution are added, the precipitate is filtered and washed with AcOEt. The organic phase is separated and washed with water and dried, giving 4-(2-(azepan-1-yl)ethyl)-4,5,6,7-tetrahydro-1-phenyl-1H-indazole (36 mg, 0.11 mmol, 63%, oil).

Workup

  1. temperatureThe mixture is refluxed for 3 hours
  2. customthe reaction by means of TLC
  3. temperatureThe mixture is cooled
  4. filtrationthe precipitate is filtered
  5. washwashed with AcOEt
  6. customThe organic phase is separated
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-f1fa7d014b8045499ef0ddaa5bc1544d
Source dataset
uspto-grants-2013_03
Patent number
US08394797B2

Reaction notes

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