Ethanolamine → HCID 19079499, compound

HRID 964050Notes

Reaction equation

HRID 964050 reaction equation
[C:1]1([O-:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Na+].O[CH2:14][CH2:15][NH2:16].Cl[CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH:24]=1.P(Cl)(Cl)Cl>C(#N)C>[C:1]1([O:11][CH2:14][CH2:15][NH:16][CH2:18][C:19]2[CH:20]=[N:21][CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[CH:24]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 24387Phosphorus trichlorideHCID 109330253-(Chloromethyl)-5-(4-fluorophenyl)pyridineHCID 23662143HCID 23662143, compound

Product 1

HCID 19079499HCID 19079499, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Analogously to Example 7 a solution of 2.3 g sodium 1-naphtholate and 2.9 g N-2-chloroethyl-N-[5-(4-fluorophenyl-3-pyridylmethyl)-amine [obtainable by reaction of 2-hydroxyethylamine with 3-chloromethyl-5-(4-fluorophenyl)-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(1-naphthyloxy)-ethyl]-N-[5-(4-fluorophenyl)-3-pyridylmethyl]-amine, m.p. 92°-94°.

Sources & evidence

ORD record
ord-e8d33ee9ceb04f839b6d15a27db3cbf3
Source dataset
uspto-grants-1998_06
Patent number
US05767132

Reaction notes

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