1,2-Dichloroethane → Hydrochloric Acid

HRID 222601Notes

Reaction equation

HRID 222601 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=O)(C)(C)C.[CH:15]1([NH2:18])[CH2:17][CH2:16]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+].[Cl:38]CCCl>C(O)(=O)C>[CH:15]1([NH:18][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:17][CH2:16]1.[ClH:38]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 69828CyclopropylamineHCID 516892Sodium BicarbonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

Product 2

HCID 313Hydrochloric AcidHCID 21973772N-Cyclopropylpiperidin-4-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 1-tert-butoxycarbonylpiperidin-4-one (1 g, 5 mmol) and cyclopropylamine (352 μl) in 15 ml of 1,2-dichloroethane is stirred at RT for 20 min after which sodium trisacetoxyborohydride (1.6 g, 7 mmol) and 0.3 ml of acetic acid are added. After having been stirred at RT for 15 h, the reaction mixture is hydrolysed with a saturated solution of sodium hydrogen carbonate and extracted with 2×50 ml of dichloromethane. The combined organic phases are washed with a saturated solution of sodium chloride, dried, filtered and evaporated. The residue is taken up in 4 ml of diethyl ether after which 8 ml of hydrochloric acid (4 N in dioxane) are added. After stirring at RT for 15 h, the precipitate is filtered off and washed with diethyl ether. The desired product is obtained as hydrochloride. Yield: 0.96 g

Workup

  1. additionare added
  2. extractionextracted with 2×50 ml of dichloromethane
  3. washThe combined organic phases are washed with a saturated solution of sodium chloride
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. additionare added
  8. stirringAfter stirring at RT for 15 h
  9. filtrationthe precipitate is filtered off
  10. washwashed with diethyl ether

Sources & evidence

ORD record
ord-be96f7733d544d38a609b517e19c6370
Source dataset
uspto-grants-2012_06
Patent number
US08207349B2

Reaction notes

Loading…