Ammonium nitrate → 1-Cyclopropylpiperidin-4-amine

HRID 1415554Notes

Reaction equation

HRID 1415554 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.Cl.CO.[N+:14]([O-])([O-])=O.[NH4+].C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[NH2:14][CH:7]1[CH2:8][CH2:9][N:4]([CH:1]2[CH2:3][CH2:2]2)[CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 22985Ammonium nitrateHCID 5003444Sodium cyanoborohydrideHCID 162276291-Cyclopropylpiperidin-4-oneHCID 21893726Hydrochloride methanol

Product 1

HCID 162276441-Cyclopropylpiperidin-4-amine

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To an ice cold solution of 2.8 g. of 1-cyclopropyl-4-piperidone in 300 ml. of absolute methanol is added 0.02 moles of a solution of hydrogen chloride-methanol, 27 g. of ammonium nitrate and 2.4 g. of sodium cyanoborohydride. The solution is stirred for 72 hours at 25° C. and then poured into dilute acetic acid. The acidic solution is washed with ether and then made basic by the addition of ammonium hydroxide. The basic solution is extracted with methylene chloride, and the organic extract dried. Concentration of the extract in vacuo gives 4-amino-1-cyclopropylpiperidine.

Workup

  1. washThe acidic solution is washed with ether
  2. additionmade basic by the addition of ammonium hydroxide
  3. extractionThe basic solution is extracted with methylene chloride
  4. extractionthe organic extract
  5. customdried
  6. extractionConcentration of the extract in vacuo

Sources & evidence

ORD record
ord-2e83fb9f468340d6acbcccf32708661c
Source dataset
uspto-grants-1977_01
Patent number
US04005208

Reaction notes

Loading…