Ethanolamine → N-[2-(2-cyanophenoxy)-ethyl]-N-(5-phenyl-3-pyridylmethyl)-amine

HRID 964047Notes

Reaction equation

HRID 964047 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl[CH2:11][CH2:12][NH:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:20]=1.OCCN.ClCC1C=NC=C(C2C=CC=CC=2)C=1.P(Cl)(Cl)Cl>C(#N)C>[C:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[O:1][CH2:11][CH2:12][NH:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:20]=1)#[N:5]

Participants

7

Reactant 5

HCID 700EthanolamineHCID 119072-HydroxybenzonitrileHCID 24387Phosphorus trichlorideHCID 110849253-(Chloromethyl)-5-phenylpyridineHCID 15511893N-2-chloroethyl-N-(5-phenyl-3-pyridylmethyl)-amine

Product 1

HCID 19079381N-[2-(2-cyanophenoxy)-ethyl]-N-(5-phenyl-3-pyridylmethyl)-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.2 g 2-hydroxy-benzonitril and 2.5 g N-2-chloroethyl-N-(5-phenyl-3-pyridylmethyl)-amine [obtainable by reaction of 2-hydroxyethylamine with 3-chloromethyl-5-phenyl-pyridine and subsequent transformation of the product to the 2-chloroethyl-compound by reaction with PCl3 ] in 200 ml of acetonitrile is stirred for 5 hours at room temperature and worked up in a conventional manner to give N-[2-(2-cyanophenoxy)-ethyl]-N-(5-phenyl-3-pyridylmethyl)-amine. Stirring with 0.5 equivalenets of oxalic acid in 100 ml ethanol gives the oxalate, m.p. 208°.

Sources & evidence

ORD record
ord-6463d9177f42491bb9619708c6e6a8a1
Source dataset
uspto-grants-1998_06
Patent number
US05767132

Reaction notes

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