Piperidine → [Phenoxy(1-piperidinyl)methylene]cyanamide

HRID 2294610Notes

Reaction equation

HRID 2294610 reaction equation
C1C=CC(O[C:8]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:9][C:10]#[N:11])=CC=1.[NH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1>ClCCl>[O:12]([C:8](=[N:9][C:10]#[N:11])[N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 21460903[Phenoxy(1-piperidinyl)methylene]cyanamideYield 81.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

a)To a stirred solution of 6 g of diphenyl cyanocarbonimidate in 50 ml of dichloromethane at room temperature were added portionwise 2.1 g of piperidine. Stirring was continued for 30 minutes at room temperature. The reaction mixture was evaporated and the residue was crystallized from 2,2'-oxybispropane. The crystals were filtered off and dried, yielding 4.6 g (80.7%) of [phenoxy(1-piperidinyl)methylene]cyanamide; mp. 85.7° C. (interm. 32).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was crystallized from 2,2'-oxybispropane
  3. filtrationThe crystals were filtered off
  4. customdried

Sources & evidence

ORD record
ord-f1f184ca04a74ed8b3a512844179c502
Source dataset
uspto-grants-1997_11
Patent number
US05688952

Reaction notes

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