Sodium Azide → 1-[4-(Heptyloxy)phenyl]methanamine

HRID 704371Notes

Reaction equation

HRID 704371 reaction equation
[N-:1]=[N+]=[N-].[Na+].Cl[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=1>O.CN(C)C=O>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][NH2:1])=[CH:8][CH:9]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 14674285p-Heptyloxybenzyl chloride

Product 1

HCID 151155341-[4-(Heptyloxy)phenyl]methanamineYield 103.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 1.25 g of sodium azide in 2.5 ml of water was added to a solution of 900 mg of p-chloromethyl(heptyloxy)benzene in 25 ml of N,N-dimethylformamide, and the mixture was stirred at 100° C. for 6 hours. After cooling, the reaction mixture was diluted with water, and the product was extracted with ether. The ether layer was washed in sequence with water and saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. A solution of the thus-obtained residual oil in 10 ml of tetrahydrofuran was added dropwise at 0° C. over 5 minutes to a suspension of 200 mg of lithium aluminum hydride in 15 ml of tetrahydrofuran. The resultant mixture was stirred at the same temperature for 1 hour and then at room temperature for 1 hour. Then, sodium sulfate decahydrate added to decompose the excess lithium aluminum hydride. The insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure to give 860 mg of p-heptyloxybenzylamine.

Workup

  1. temperatureAfter cooling
  2. extractionthe product was extracted with ether
  3. washThe ether layer was washed in sequence with water and saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionA solution of the thus-obtained residual oil in 10 ml of tetrahydrofuran was added dropwise at 0° C. over 5 minutes to a suspension of 200 mg of lithium aluminum hydride in 15 ml of tetrahydrofuran
  7. stirringThe resultant mixture was stirred at the same temperature for 1 hour
  8. waitat room temperature for 1 hour
  9. additionThen, sodium sulfate decahydrate added
  10. filtrationThe insoluble matter was filtered off
  11. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d7afed0f174d49d3bec44f483304f6be
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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