Sodium Hydroxide → HCID 22177248, compound

HRID 1797172Notes

Reaction equation

HRID 1797172 reaction equation
[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)C#N.[H-].[H-].[H-].[H-].[Li+].[Al+3].C[OH:28].C(Cl)Cl.[OH-].[Na+]>C1COCC1.O>[CH3:1][N:2]([CH3:20])[CH2:3][CH2:4][CH:5]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=1)[OH:28]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 21226129Dichloromethane methanolHCID 21226445Aluminium lithium hydrideHCID 22177239HCID 22177239, compound

Product 1

HCID 22177248HCID 22177248, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-dimethylamino-2-(4-pyridin-4-yl-phenyl)-butyronitrile (680 mg, 2.56 mmol) in THF (5 mL) was added LiAlH4 (1M in THF, 26 mL, 26 mmol) and the mixture was stirred at room temperature for 16 h. TLC (10% MeOH/CH2Cl2) showed no starting material left and a new low Rf spot was formed. The mixture was treated with 1.74 mL of H2O, followed by 3.48 mL of 1N aqueous NaOH, and then 5.2 mL of H2O. After 30 min of stirring, the mixture was filtered and the filtrate was dried over Na2SO4 and concentrated to give 3-dimethylamino-1-(4-pyridin-4-yl-phenyl)-propan-1-ol as a yellowish solid, 300 mg (46%). 1H NMR (300 MHz, CDCl3): δ 8.75 (dd, 2H), 7.74 (m, 2H), 7.62 (m, 4H), 5.12 (dd, 1H), 2.82 (m, 1H), 2.64 (m, 1H), 2.44 (s, 6H), 1.97 (m, 2H).

Workup

  1. waitleft
  2. customa new low Rf spot was formed
  3. stirringAfter 30 min of stirring
  4. filtrationthe mixture was filtered
  5. dry with materialthe filtrate was dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3075aef0666743578f46c6d507ee501b
Source dataset
uspto-grants-2006_04
Patent number
US07034056B2

Reaction notes

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