Reaction #1726726

Reaction equation

3,3-diphenylpropylamine

sodium triacetoxyborohydride

acetic acid

N-Boc-piperidone

→

yellow solid

Yield 101.4%

tert-butyl 4-[(3,3-diphenylpropyl)amino]-1-piperidine carboxylate

Yield 101.4%

Solvents

dichloroethane

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture is agitated for 30 minutes
2. 2
   WashThe organic phase is washed with a saturated solution of sodium bicarbonate, with sodium chloride
3. 3
   Dryingdried over magnesium sulphate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in order

Procedure

3,3-diphenylpropylamine (5.8 g, 27.5 mmol), sodium triacetoxyborohydride (6.36 g, 30 mmol) and 0.5 ml of acetic acid are added to 5 g (25 mmol) of N-Boc-piperidone in 100 ml of dry dichloroethane. The turbid yellow solution is agitated at ambient temperature for 1 hour. 50 ml of a soda solution (0.1 M) is then added and the mixture is agitated for 30 minutes. The organic phase is washed with a saturated solution of sodium bicarbonate, with sodium chloride, dried over magnesium sulphate, filtered and concentrated in order to produce 10 g of a yellow solid. This solid is purified by flash chromatography on silica gel eluting with a heptane/ethyl acetate mixture (4/1, 3/1, 2/1 then 1/1) then with pure ethyl acetate. The fractions are concentrated under vacuum in order to produce 5.6 g (yield=57%) of a pale yellow solid.

Source