Methanimidic acid, N-cyano-, ethyl ester → N-cyano-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]formamidine hydrochloride

HRID 745852Notes

Reaction equation

HRID 745852 reaction equation
[N:1]1([CH2:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[O:11][CH2:12][CH2:13][CH2:14][NH2:15])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:19]([N:21]=[CH:22]OCC)#[N:20].[ClH:26].C(O)C>C(O)C.C(OCC)C>[ClH:26].[C:19]([NH:21][CH:22]=[N:15][CH2:14][CH2:13][CH2:12][O:11][C:10]1[CH:16]=[CH:17][CH:18]=[C:8]([CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:9]=1)#[N:20]

Participants

6

Reactant 3

HCID 9920370Methanimidic acid, N-cyano-, ethyl esterHCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 21887872Ethanol hydrochloride

Product 1

HCID 23312557N-cyano-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]formamidine hydrochloride

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 2.48 g of 3-[3-(1-piperidinylmethyl)phenoxy]-1-propanamine (prepared according to British Pat. No. 2,023,123 which is hereby incorporated by reference) in 25 ml of absolute ethanol, are added dropwise 0.98 g of ethyl N-cyano-formimidate in 15 ml of ethanol, under stirring and at room temperature. Stirring is maintained for 30 minutes, and then the ethanol is removed by underpressure distillation. An oil residue is formed, which is then dissolved in 250 ml of ethyl ether, after which 0.95 ml of 10N HCl/ethanol are added, yielding 1.4 g of N-cyano-N'-[3-[3-(1-piperidinylmethyl)phenoxy]propyl]formamidine hydrochloride.

Workup

  1. stirringStirring
  2. temperatureis maintained for 30 minutes
  3. customthe ethanol is removed by underpressure distillation
  4. customAn oil residue is formed

Sources & evidence

ORD record
ord-f71b7aba58ad41a5b63dce9f712a6e90
Source dataset
uspto-grants-1986_07
Patent number
US04600780

Reaction notes

Loading…