3-Amino-1-propanol → HCID 19079352, compound

HRID 964048Notes

Reaction equation

HRID 964048 reaction equation
[C:1]1([O-:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].Cl[CH2:10][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][C:24]([F:27])=[CH:23][CH:22]=2)[CH:20]=1.OCCCN.ClCC1C=NC=C(C2C=CC(F)=CC=2)C=1.P(Cl)(Cl)Cl>C(#N)C>[O:7]([CH2:10][CH2:11][CH2:12][NH:13][CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([C:21]2[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=2)[CH:20]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 5

HCID 90863-Amino-1-propanolHCID 24387Phosphorus trichlorideHCID 4445035Phenolate SodiumHCID 109330253-(Chloromethyl)-5-(4-fluorophenyl)pyridineHCID 19079504N-3-chloropropyl-N-[5-(4-fluorophenyl)-3-pyridylmethyl]-amine

Product 1

HCID 19079352HCID 19079352, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Analogously to Example 7 a solution of 2.3 g sodium phenolate and 2.5 g N-3-chloropropyl-N-[5-(4-fluorophenyl)-3-pyridylmethyl]-amine [obtainable by reaction of 3-hydroxypropylamine with 3-chloromethyl-5-(4-fluorophenyl)-pyridine and subsequent transformation of the product to the 3-chloropropyl-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-(3-phenoxy-propyl)-N-[5-(4-fluorophenyl)-3-pyridyl-methyl]-amine. Stirring with Q5 equivalents of oxalic acid in 100 ml ethanol/water mixture gives the oxalate-hemihydrate, m.p. 217°.

Sources & evidence

ORD record
ord-0f597c166fd4421c9ec10b4918b1bd12
Source dataset
uspto-grants-1998_06
Patent number
US05767132

Reaction notes

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