5-Aminovaleric acid → HCID 11978855, compound

HRID 657623Notes

Reaction equation

HRID 657623 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(=O)C([O-])=O.[NH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28](O)=O.[OH-].[Na+]>O>[N:11]1([CH2:10][CH2:9][CH2:8][O:1][C:2]2[CH:7]=[CH:6][C:5]([C:28]3[CH2:27][CH2:26][CH2:25][CH2:24][N:23]=3)=[CH:4][CH:3]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 1385-Aminovaleric acidHCID 14798Sodium HydroxideHCID 71081OxalateHCID 2057368HCID 2057368, compound

Product 1

HCID 11978855HCID 11978855, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-(3-phenoxypropyl)piperidine, oxalate (0.2 g), 5-aminopentanoic acid (0.076 g) and polyphosphoric acid (2 g) is stirred at a temperature close to 100° C. for one hour. The mixture is cooled to room temperature, diluted with water (25 mL), made alkaline through addition of concentrated aqueous sodium hydroxide solution with external cooling and extracted twice with ethyl acetate (25 mL). The organic layers are pooled, washed with a saturated aqueous solution of sodium chloride (25 mL), dried over magnesium sulphate and purified by chromatography over silica gel. Fractions containing the expected product are pooled, concentrated under reduced pressure to give 0.172 g of 6-[4-(3-piperidinopropoxy)phenyl]-2,3,4,5-tetrahydropyridine which is dissolved in ethanol (2 mL). A solution of oxalic acid (0.104 g) in ethanol (0.5 mL) is added. The precipitate that appears on standing is filtered, rinsed with ethanol and dried to afford 200 mg of 6-[4-(3-piperidinopropoxy)phenyl]-2,3,4,5-tetrahydropyridine, oxalate as a white powder melting at 104° C.

Workup

  1. customclose to 100° C. for one hour
  2. temperaturewith external cooling
  3. extractionextracted twice with ethyl acetate (25 mL)
  4. washwashed with a saturated aqueous solution of sodium chloride (25 mL)
  5. dry with materialdried over magnesium sulphate
  6. custompurified by chromatography over silica gel
  7. additionFractions containing the expected product
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a47fc9583af543d6abd724edca09ab1a
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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