Sodium Sulfate → 4-(Tetradecyloxy)benzenemethanamine

HRID 248007Notes

Reaction equation

HRID 248007 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:21][C:22]1[CH:30]=[CH:29][C:25]([C:26]([NH2:28])=O)=[CH:24][CH:23]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:7]([O:21][C:22]1[CH:30]=[CH:29][C:25]([CH2:26][NH2:28])=[CH:24][CH:23]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 12361468HCID 12361468, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 117234984-(Tetradecyloxy)benzenemethanamineYield 96.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a room temperature mixture of 3.64 g of lithium aluminum hydride in 300 ml of dry tetrahydrofuran is added a hot solution of 15.98 g of product from Example 98 in 150 ml of tetrahydrofuran. The reaction is stirred at room temperature for 20 hours, refluxed for 8 hours and stirred at room temperature for 50 hours. The reaction is treated with saturated sodium sulfate, filtered and concentrated to give 14.77 g of the desired product as colorless crystals.

Workup

  1. temperaturerefluxed for 8 hours
  2. stirringstirred at room temperature for 50 hours
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-adbeb04618f34d1cbd999d5b071b4634
Source dataset
uspto-grants-1993_05
Patent number
US05208247

Reaction notes

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