2-Bromopyridine → 2-[2-(4-Hydroxy-4-(2-pyridyl)-piperidino)-ethyl]-1,4-benzodioxan dihydrochloride

HRID 1391070Notes

Reaction equation

HRID 1391070 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Li])CCC.[O:13]=[C:14]1[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH:22]2[O:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[O:24][CH2:23]2)[CH2:16][CH2:15]1.[Cl-:32].[NH4+]>O1CCCC1.CCCCCC>[ClH:32].[ClH:32].[OH:13][C:14]1([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][CH:22]2[O:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[O:24][CH2:23]2)[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 79732-BromopyridineHCID 25517Ammonium ChlorideHCID 205401701-[2-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethyl]piperidin-4-oneHCID 178418339Butyllithium

Product 1

HCID 213319852-[2-(4-Hydroxy-4-(2-pyridyl)-piperidino)-ethyl]-1,4-benzodioxan dihydrochloride

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To the solution of 3.2 g of 2-bromopyridine in 50 ml of tetrahydrofuran is added 12.5 ml of 1.6 N n-butyl lithium in hexane, while stirring at -75°. After one hour the solution of 2.65 g of 2-[2-(4-oxopiperidino)-ethyl]-1,4-benzodioxan in 10 ml of tetrahydrofuran is added while stirring. After standing overnight at room temperature, the mixture is decomposed with 10 ml of saturated aqueous ammonium chloride. The organic solvent layer is separated, dried, evaporated and the residue strongly basified with aqueous ammonium hydroxide. The mixture is extracted with ethyl acetate, the extract washed with water, dried and evaporated. The residue is suspended in 10 ml of ethanol, the suspension neutralized with ethanolic hydrogen chloride and the precipitate recrystallized from ethanol-diethyl ether, to yield the 2-[2-(4-hydroxy-4-(2-pyridyl)-piperidino)-ethyl]-1,4-benzodioxan dihydrochloride, melting at 260°-262° with decomposition.

Workup

  1. stirringwhile stirring
  2. customThe organic solvent layer is separated
  3. customdried
  4. customevaporated
  5. extractionThe mixture is extracted with ethyl acetate
  6. washthe extract washed with water
  7. customdried
  8. customevaporated
  9. customthe precipitate recrystallized from ethanol-diethyl ether

Sources & evidence

ORD record
ord-f20441da55e44debbbb677a9ead17890
Source dataset
uspto-grants-1979_02
Patent number
US04140781

Reaction notes

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