Acetone → N-Isopropylcyclopentanamine

HRID 1700103Notes

Reaction equation

HRID 1700103 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH:15]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16]1.[CH3:21][C:22]([CH3:24])=O>>[CH:22]([NH:20][CH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1)([CH3:24])[CH3:21]

Participants

4

Reactant 3

HCID 180AcetoneHCID 2906CyclopentylamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 17750362N-Isopropylcyclopentanamine

Procedure

Sodium triacetoxyborohydride (33.76 g, 0.16 mol) was added to a solution of cyclopentylamine (15 ml, 0.15 mol) in acetone (500 ml). The reaction mixture was stirred at room temperature for 24 hr then the solvent was removed and the reaction mixture was partitioned between ethyl acetate (400 ml) and 2M aqueous sodium hydroxide (150 ml). The organic layer was separated, dried (anhydrous magnesium sulphate) and evaporated under reduced pressure to give the title compound (12 g) as a liquid.

Workup

  1. customthe solvent was removed
  2. customthe reaction mixture was partitioned between ethyl acetate (400 ml) and 2M aqueous sodium hydroxide (150 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (anhydrous magnesium sulphate)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fb66345f717e46e2a5e40d623bd3661b
Source dataset
uspto-grants-2002_02
Patent number
US06350735B1

Reaction notes

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