Water → [4-(Tetradecyloxy)phenyl methyl]aminobenzenemethanol

HRID 484634

Reaction equation

HRID 484634 reaction equation
OC[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:39](OCC)(=[O:41])C.O>O1CCCC1>[CH2:18]([O:17][C:14]1[CH:13]=[CH:12][C:11]([CH2:10][NH:9][C:6]2[CH:5]=[CH:4][CH:3]=[CH:8][C:7]=2[CH2:39][OH:41])=[CH:16][CH:15]=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 86745365[4-(Tetradecyloxy)phenyl methyl]aminobenzenemethanol

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-9bc4211be5eb438ab5e000e0f15fc582
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Linked notes

Loading…