Water → 4-[[[4-(Tetradecyloxy)phenyl]methyl]amino]benzenemethanol

HRID 483596

Reaction equation

HRID 483596 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=O)[C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.O>O1CCCC1>[CH2:18]([O:17][C:14]1[CH:15]=[CH:16][C:11]([CH2:10][NH:9][C:6]2[CH:7]=[CH:8][C:3]([CH2:2][OH:1])=[CH:4][CH:5]=2)=[CH:12][CH:13]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10410958N-[4-(Hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 100025504-[[[4-(Tetradecyloxy)phenyl]methyl]amino]benzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 13 g of N-[4-(hydroxymethyl)phenyl]-4-(tetradecyloxy)benzamide in 250 ml of tetrahydrofuran is added dropwise with stirring under argon 59.14 ml of 1 molar lithium aluminum hydride in tetrahydrofuran. The mixture is stirred at room temperature for 0.5 hours and refluxed for 5 hours. Ethyl acetate is added dropwise followed by water. The mixture is filtered and the cake washed with ether. The filtrate is evaporated to a residue which is purified by chromatography on silica gel with 2:1 chloroform:hexane to give the desired product.

Workup

  1. additionis added dropwise
  2. temperaturerefluxed for 5 hours
  3. filtrationThe mixture is filtered
  4. washthe cake washed with ether
  5. customThe filtrate is evaporated to a residue which
  6. customis purified by chromatography on silica gel with 2:1 chloroform

Sources & evidence

ORD record
ord-9a1eb69f38f44cb9bfe158ba5f2f6ea5
Source dataset
uspto-grants-1993_07
Patent number
US05225425

Linked notes

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