Ammonia → l-Amino-1-cyano-2-(1-methyl-piperid-4-yl)-ethane

HRID 586148Notes

Reaction equation

HRID 586148 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([CH2:8][CH:9]=O)[CH2:4][CH2:3]1.[C-:11]#[N:12].[Na+].[NH4+:14].[Cl-].N.CO.N>CO>[NH2:14][CH:9]([C:11]#[N:12])[CH2:8][CH:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1

Participants

7

Reactant 5

HCID 222AmmoniaHCID 8929Sodium CyanideHCID 25517Ammonium ChlorideHCID 21666286(1-Methylpiperidin-4-yl)acetaldehydeHCID 21705897Ammonia methanol

Product 1

HCID 22329405l-Amino-1-cyano-2-(1-methyl-piperid-4-yl)-ethane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above aldehyde (1 equiv) is mixed with NaCN (1.1 equiv) and NH4Cl (1.1 cquiv) in 2 Molar NH3/MeOH (4 equiv NH3). The flask is fitted with a reflux condenser and the mixture is refluxed. At the end of each of the first 3 h an additional equivalent of NH3 in MeOH is added. The reaction mixture is cooled and the excess solids are filtered away on a frit. The filtrate is concentrated by rotary evaporation and the residue is triturated with diethyl ether and the mixture is filtered again. The filtrate is concentrated on a rotovap. The product is purified, if necessary, by flash chromatography on silica with EtOAc/hexanes as an eluent to yield 1-amino-1-cyano-2-(1-methyl-piperid-4-yl)-ethane.

Workup

  1. customThe flask is fitted with a reflux condenser
  2. temperaturethe mixture is refluxed
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe excess solids are filtered away on a frit
  5. concentrationThe filtrate is concentrated by rotary evaporation
  6. customthe residue is triturated with diethyl ether
  7. filtrationthe mixture is filtered again
  8. concentrationThe filtrate is concentrated on a rotovap
  9. customThe product is purified

Sources & evidence

ORD record
ord-52b50f1ea85b4acb994001a2fb9f34c5
Source dataset
uspto-grants-2005_08
Patent number
US06936606B2

Reaction notes

Loading…