Isobutylamine → N-(2-methylpropyl)cyclopentanamine

HRID 1746667

Reaction equation

HRID 1746667 reaction equation
[C:1]1(=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([NH2:11])[CH:8]([CH3:10])[CH3:9].[BH4-].[Na+]>C(O)C>[CH:1]1([NH:11][CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 8452CyclopentanoneHCID 4311764Sodium borohydride

Product 1

HCID 28428761N-(2-methylpropyl)cyclopentanamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of cyclopentanone (10 g, 0.12 mol) and isobutyl amine (29.5 ml, 0.297 mol) was heated at 70° C. for 3 h under nitrogen. After cooling to 0° C., absolute ethanol (50 ml) was added to the reaction mixture, followed by sodium borohydride (6.59 g, 0.178 mol) in portions. The reaction mixture stirred at RT for 12 h, the solvent was removed under vacuum. The residue was taken up in MTBE and washed with water and brine. The organic layer was dried over Na2SO4, evaporated to dryness and the crude was purified by chromatography using silica gel (60-120 mesh), dichloromethane\methanol as eluent to afford of the titled compound as a yellow liquid.

Workup

  1. temperatureAfter cooling to 0° C.
  2. customthe solvent was removed under vacuum
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated to dryness
  6. customthe crude was purified by chromatography

Sources & evidence

ORD record
ord-ceeb79036c2d462eb3adb7c1564a91c0
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Linked notes

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