Sodium Hydroxide → 1-Phenyl-cyclopropylamine

HRID 911320Notes

Reaction equation

HRID 911320 reaction equation
[C:1]1([C:7]2(C(O)=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N-:13]=[N+]=[N-].[Na+].[OH-].[Na+]>S(=O)(=O)(O)O.C(Cl)Cl>[C:1]1([C:7]2([NH2:13])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 33557Sodium AzideHCID 802061-Phenylcyclopropanecarboxylic acid

Product 1

HCID 1945491-Phenyl-cyclopropylamineYield 54%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 1-phenyl-cyclopropanecarboxylic acid (2.5 g, 15.4 mmol) in a mixture of sulfuric acid (12.5 mL) and DCM (25 mL). Add sodium azide (2.3 g, 35.4 mmol) by small portions at ambient temperature. Heat the reaction mixture at 50° C. for 8 h, cool to 0° C. and slowly add 2M aqueous NaOH until pH 11. Extract the reaction mixture with DCM (3×100 mL), combine the organic extracts and dry over anhydrous Na2SO4. Evaporate the solvent and purify by chromatography on silica gel eluting with DCM and DCM/2M ammonia in methanol (9:1) to obtain the title compound as a brown oil (1.1 g, 54%). MS (ES+) m/z: 134 (M+H)+.

Workup

  1. customat ambient temperature
  2. temperaturecool to 0° C.
  3. extractionExtract the reaction mixture with DCM (3×100 mL)
  4. dry with materialdry over anhydrous Na2SO4
  5. customEvaporate the solvent
  6. custompurify by chromatography on silica gel eluting with DCM and DCM/2M ammonia in methanol (9:1)

Sources & evidence

ORD record
ord-8f7b9ee17979418ebe30f6ef0248cb95
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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