Hydrochloric Acid → 4-(2-Dimethylaminoethyl)-1-(3-phenoxypropyl)piperidine dihydrochloride

HRID 962449

Reaction equation

HRID 962449 reaction equation
C([Li])CCC.[Br-].[CH3:7][N:8]([CH3:30])[CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O:31]([CH2:38][CH2:39][CH2:40][N:41]1[CH2:46][CH2:45][C:44](=O)[CH2:43][CH2:42]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[ClH:48]>C1COCC1.CCOCC.[Pd]>[ClH:48].[ClH:48].[CH3:7][N:8]([CH3:30])[CH2:9][CH2:10][CH:44]1[CH2:45][CH2:46][N:41]([CH2:40][CH2:39][CH2:38][O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:42][CH2:43]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 2724136(2-(Dimethylamino)ethyl)triphenylphosphonium bromideHCID 180022221-(3-Phenoxypropyl)piperidin-4-oneHCID 178418339Butyllithium

Product 1

HCID 190854914-(2-Dimethylaminoethyl)-1-(3-phenoxypropyl)piperidine dihydrochloride

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

In a similar manner to Example 28, n-butyllithium (25.2 ml, 2.5M solution in hexanes) was added to a suspension of (2-dimethylaminoethyl)triphenylphosphonium bromide (28.7 g) in dry THF (200 ml). This mixture was then treated with a solution of 1-(3-phenoxypropyl)-4-piperidone (14.7 g) in THF (20 ml). The oil obtained after work up (6.24 g) was hydrogenated in IMS at 1 atmosphere over 10% palladium charcoal over 16 hours. The catalyst was removed by filtration. The filtrate was evaporated and the residue was dissolved in petroleum ether, b.p. 60°-80° C. The solution was dried and evaporated to give an oil which was dissolved in ether and acidified with ethereal hydrogen chloride to yield a precipitate. The precipitate was collected by filtration and recrystallised from IMS to give 4-(2-dimethylaminoethyl)-1-(3-phenoxypropyl)piperidine dihydrochloride, m.p. 294°-295° C.

Workup

  1. customThe oil obtained after work up (6.24 g)
  2. customThe catalyst was removed by filtration
  3. customThe filtrate was evaporated
  4. dissolutionthe residue was dissolved in petroleum ether
  5. customThe solution was dried
  6. customevaporated
  7. customto give an oil which
  8. customto yield a precipitate
  9. filtrationThe precipitate was collected by filtration
  10. customrecrystallised from IMS

Sources & evidence

ORD record
ord-4b8dc02404704dde86b51b67f074d2ad
Source dataset
uspto-grants-1998_06
Patent number
US05760035

Linked notes

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