Water → 5-Benzyl-5-azaspiro[2.4]heptan-7-amine

HRID 1721091Notes

Reaction equation

HRID 1721091 reaction equation
[CH2:1]([N:8]1[CH2:14][C:13](=[N:15]O)[C:10]2([CH2:12][CH2:11]2)[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:15][CH:13]1[C:10]2([CH2:12][CH2:11]2)[CH2:9][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:14]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 73885721CID 73885721

Product 1

HCID 108565665-Benzyl-5-azaspiro[2.4]heptan-7-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 80 ml of dry tetrahydrofuran was dissolved 490 mg of compound 5 followed by addition of 500 mg of lithium aluminum hydride and the mixture was refluxed for 8 hours. Then, at room temperature, 0.5 ml of water, 0.5 ml of 15% aqueous sodium hydroxide and 1.5 ml of water were added thereto in the order mentioned and the insolubles were filtered off. The filtrate was concentrated under reduced pressure to give 7-amino-5-benzyl-5-azaspiro[2.4]heptane (compound 6). This product was dissolved as it was, i.e., without purification, in 20 ml of ethanol and after addition of 10% palladium-on-carbon, catalytic hydrogenation was carried out at 4.5 kg/cm2 and 50° C. After 6 hours of reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure at a temperature not higher than room temperature. The above procedure gave title compound 7 as a crude product. This compound 7 was used, without purification, in various reactions.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. filtrationthe insolubles were filtered off
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-16257e1cc557421b823d14a27459df76
Source dataset
uspto-grants-1996_04
Patent number
US05508428

Reaction notes

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