Mechlorethamine → 1-Methylpiperidine-4,4-dicarbonitrile

HRID 651738Notes

Reaction equation

HRID 651738 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:6][CH2:7]Cl)[CH3:5].C(#N)[CH:10]([CH2:12][C:13]#[N:14])O.C(=O)([O-])[O-].[K+].[K+].C(#[N:24])C>>[CH3:5][N:4]1[CH2:6][CH2:7][C:12]([C:10]#[N:24])([C:13]#[N:14])[CH2:2][CH2:3]1

Participants

5

Reactant 4

HCID 4033MechlorethamineHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 150578121-Methylpiperidine-4,4-dicarbonitrile

Procedure

A mixture of 31.2 g of bis(chloroethyl)methylamine, 13.2 g of malonitrile, 55.28 g of potassium carbonate and 800 ml of acetonitrile is refluxed on a steam bath for 24 hours, then filtered while hot. The filtrate is evaporated and the residue crystallized with charcoal treatment from 100 ml of ethanol, giving 10.6 g of 1-methylpiperidine-4,4-dicarbonitrile, as colorless crystals.

Workup

  1. temperatureis refluxed on a steam bath for 24 hours
  2. filtrationfiltered while hot
  3. customThe filtrate is evaporated
  4. customthe residue crystallized with charcoal treatment from 100 ml of ethanol

Sources & evidence

ORD record
ord-62fad379993c41b3939585a365c75edf
Source dataset
uspto-grants-2001_08
Patent number
US06281365B1

Reaction notes

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