3-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine → 5-Nitro-2-[3-(3-piperidinomethylphenoxy)propylamino]-4(3H)-pyrimidone

HRID 622782Notes

Reaction equation

HRID 622782 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.CS[C:21]1[N:26]=[C:25]([OH:27])[C:24]([N+:28]([O-:30])=[O:29])=[CH:23][N:22]=1>C(O)C>[N+:28]([C:24]1[C:25](=[O:27])[NH:26][C:21]([NH:15][CH2:14][CH2:13][CH2:12][O:11][C:10]2[CH:16]=[CH:17][CH:18]=[C:8]([CH2:7][N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:9]=2)=[N:22][CH:23]=1)([O-:30])=[O:29]

Participants

4

Reactant 2

HCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 178503473C5H5N3O3S

Product 1

HCID 143266955-Nitro-2-[3-(3-piperidinomethylphenoxy)propylamino]-4(3H)-pyrimidone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-(3-piperidinomethylphenoxy)propylamine (8.20 g; 33.0 mmoles) and 2-methylthio-5-nitro-4-hydroxypyrimidine (6.20 g; 32.5 mmoles) [prepared according to the procedure described in U.S. Pat. No. 4,241,056] in 35 ml of ethanol was stirred at reflux temperature for 18 hours. The reaction mixture was evaporated under reduced pressure, and the residue was placed on 250 g of silica gel (230-400 mesh) and chromatographed by flash chromatography using a gradient elution of methanol-methylene chloride. The appropriate fractions were combined and evaporated, and the product was recrystallized from tetrahydrofuran to give the title compound, mp 161°-164° C.

Workup

  1. temperatureat reflux temperature for 18 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customchromatographed by flash chromatography
  4. washa gradient elution of methanol-methylene chloride
  5. customevaporated
  6. customthe product was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-7c4e2fa1cddc43e3a5be58879bb5ddcd
Source dataset
uspto-grants-1988_09
Patent number
US04772704

Reaction notes

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