3-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amine → HCID 20186011, compound

HRID 2309195Notes

Reaction equation

HRID 2309195 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.[N+](N[C:23]1[NH:28][C:27](=[O:29])[C:26]([O:30][CH2:31][CH3:32])=[CH:25][N:24]=1)([O-])=O>N1C=CC=CC=1>[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][NH:15][C:23]2[NH:28][C:27](=[O:29])[C:26]([O:30][CH2:31][CH3:32])=[CH:25][N:24]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 102205613-(3-(Piperidin-1-ylmethyl)phenoxy)propan-1-amineHCID 20186008HCID 20186008, compound

Product 1

HCID 20186011HCID 20186011, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-[3-(Piperidinomethyl)phenoxy]propylamine (1.64 g), 2-nitroamino-5-ethoxypyrimidin-4-one (1.2 g) and pyridine (15 ml) were stirred under reflux conditions for 18 hours. Pyridine was evaporated under reduced pressure and water (25 ml) and chloroform (25 ml) added. The mixture was shaken, the chloroform layer extracted; the aqueous layer was further extracted with chloroform (2×25 ml), and the combined chloroform extracts were washed with water, dried (MgS04) and evaporated under reduced pressure. The resultant residue was subjected to column chromatography on silica gel using chloroform: methanol (95:5) as eluant. The desired fractions were evaporated to give the title product as a residue. This residue was washed with diethyl ether and dissolved in isopropanol. This solution was treated with maleic acid (0.77 g) in isopropanol to give a solid maleate salt which on crystallisation from ethanol gave 2-[3-[3-(piperidinomethyl)phenoxy]propylamino ]-5-ethoxypyrimidin-4-one dimaleate (1.11 g), m.p. 68°-71° C.

Workup

  1. customPyridine was evaporated under reduced pressure and water (25 ml) and chloroform (25 ml)
  2. additionadded
  3. extractionthe chloroform layer extracted
  4. extractionthe aqueous layer was further extracted with chloroform (2×25 ml)
  5. washthe combined chloroform extracts were washed with water
  6. customdried (MgS04)
  7. customevaporated under reduced pressure
  8. customThe desired fractions were evaporated

Sources & evidence

ORD record
ord-826fdf31cc944edf9744cf918d81ddca
Source dataset
uspto-grants-1987_09
Patent number
US04694008

Reaction notes

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