1-Phenylcyclopropanecarboxamide → 1-Phenylcyclopropanemethanamine

HRID 1685317Notes

Reaction equation

HRID 1685317 reaction equation
[C:1]1([C:7]2([C:10]([NH2:12])=O)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[C:1]1([C:7]2([CH2:10][NH2:12])[CH2:8][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2922171-PhenylcyclopropanecarboxamideHCID 21226445Aluminium lithium hydride

Product 1

HCID 702871-PhenylcyclopropanemethanamineYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A solution of 1-phenylcyclopropanecarboxamide (0.450 g, 2.79 mmol) in tetrahydrofuran (5 mL) was slowly added to a suspension of LAH (0.117 g, 3.07 mmol) in tetrahydrofuran (5 mL) at 23° C. over 2 minutes. The reaction was then heated to 65° C. for 6 hours. The reaction was quenched with the Rochelle salt (1N in water, 10 mL) and extracted with ethyl acetate (3×). The combined organic layers were then dried over anhydrous magnesium sulfate, filtered and concentrated to give the crude title material (0.200 g, 49%) as an oil which was used as such in the next reaction. An aliquot was purified on preparative HPLC (ammonium acetate/water/acetonitrile). 1H NMR (400 MHz, CDCl3, acetic acid salt) δ: 0.83-0.94 (4H, m), 1.98 (3H, s), 2.90 (2H, s), 4.98 (3H, br s), 7.23-7.37 (5H, m).

Workup

  1. customThe reaction was quenched with the Rochelle salt (1N in water, 10 mL)
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialThe combined organic layers were then dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fab299aae0f546779a72abe5a7e82cf8
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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