Sodium Azide → 1-Phenyl-cyclopropylamine

HRID 14056

Reaction equation

HRID 14056 reaction equation
[N-:1]=[N+]=[N-].[Na+].[C:5]1([C:11]2(C(O)=O)[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>S(=O)(=O)(O)O.ClCCl>[C:5]1([C:11]2([NH2:1])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 802061-Phenylcyclopropanecarboxylic acid

Product 1

HCID 1945491-Phenyl-cyclopropylamine

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Following the procedure described in N. W. Werner et. al., J. Org. Syn. Coll. Vol. 5, 273-276, sodium azide (0.915 g, 14.1 mmol) is slowly added to a solution of 1-phenyl-cyclopropanecarboxlic acid (1.0 g, 6.1 mmol) in concentrated sulfuric acid (5 ml) and dichloromethane (10 ml). The sodium sulfate precipitated out of solution. The reaction mixture is heated to 50 degrees C. for 17 hours and then cooled to 0 degrees C. The mixture is basified to pH=11 with sodium hydroxide (1N) and extracted with dichloromethane (2×). The organic layers are combined, dried over sodium sulfate, filtered and concentrated. The residue is purified by chromatography (silica gel; isopropyl alcohol/chloroform/ammonium hydroxide 4/95/1) to give the title compound, MS (ESI+) for C9H11N m/z (M+H)+=134.

Workup

  1. customThe sodium sulfate precipitated out of solution
  2. temperaturecooled to 0 degrees C
  3. extractionextracted with dichloromethane (2×)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue is purified by chromatography (silica gel; isopropyl alcohol/chloroform/ammonium hydroxide 4/95/1)

Sources & evidence

ORD record
ord-b6b12c4b583a4f42ba7d7ac0bdcfa0de
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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