Tetrahydrofuran → HCID 44224242, compound

HRID 76941Notes

Reaction equation

HRID 76941 reaction equation
[CH3:1][N:2]([CH3:31])[C:3]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:8][CH2:7][C:6]([N:15]([CH3:24])[C:16](=O)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:5][CH2:4]1.C1COCC1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[CH2:16]([N:15]([CH3:24])[C:6]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:8][C:3]([N:2]([CH3:31])[CH3:1])([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:4][CH2:5]1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 68631670N-(4-dimethylamino-1,4-diphenyl-cyclohexyl)-N-methyl-benzamide

Product 1

HCID 44224242HCID 44224242, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound from step 1 (160 mg, 0.387 mmol) was dissolved in abs. THF (15 mL) and mixed with LiAlH4 (29 mg, 0.775 mmol) in argon. The batch was boiled for 7 h with reflux and then cooled to room temperature. THF (5 mL) and H2O (5 mL) were added to the batch with ice cooling and subsequently stirred for 30 min. The batch was filtered over a fitted glass filter with diatomaceous earth and subsequently rinsed with dichloromethane (50 mL). The combined filtrates were concentrated to low volume in vacuum.

Workup

  1. temperaturewith reflux
  2. filtrationThe batch was filtered over a fitted glass
  3. filtrationfilter with diatomaceous earth
  4. washsubsequently rinsed with dichloromethane (50 mL)
  5. concentrationThe combined filtrates were concentrated to low volume in vacuum

Sources & evidence

ORD record
ord-58d69b55385c40fcb60021d230136f8b
Source dataset
uspto-grants-2014_09
Patent number
US08835689B2

Reaction notes

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