Water → HCID 69432196, compound

HRID 1269817Notes

Reaction equation

HRID 1269817 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([O:10][C@H:11]3[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18](=O)[CH3:19])[CH2:12]3)=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[CH2:18]([NH:17][C@H:13]1[CH2:14][CH2:15][CH2:16][C@H:11]([O:10][C:6]2[CH:5]=[C:4]3[C:9](=[CH:8][CH:7]=2)[NH:1][N:2]=[CH:3]3)[CH2:12]1)[CH3:19]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 69432514HCID 69432514, compound

Product 1

HCID 69432196HCID 69432196, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The trans-N-[3-(1H-indazol-5-yloxy)cyclohexyl]-acetamide (0.077 g, 0.28 mmol) obtained in Example 398 was added to a suspension of lithium aluminum hydride (0.040 g, 1.05 mmol) in tetrahydrofuran (5 ml) and stirred for 12 hours with heating under reflux. The resulting solution was cooled on an ice bath, followed by adding dropwise thereto water (0.05 ml), a 2N-aqueous sodium hydroxide solution (0.10 ml) and water (0.15 ml) in that order. Thereafter, the insoluble material was removed by filtration using Celite. The filtrate was purified by a silica gel chromatography (eluent: chloroform/methanol/30%-aqueous ammonia=10/1/0 to 100/10/1) to obtain trans-N-ethyl-3-(1H-indazol-5-yloxy)cyclohexanamine (0.060 g, 83%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux
  3. temperatureThe resulting solution was cooled on an ice bath
  4. additionby adding dropwise
  5. customThereafter, the insoluble material was removed by filtration
  6. customThe filtrate was purified by a silica gel chromatography (eluent: chloroform/methanol/30%-aqueous ammonia=10/1/0 to 100/10/1)

Sources & evidence

ORD record
ord-d838a2bd6a8e41dda06f29d15b9cdbea
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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