Ammonium Chloride → 2-[2-(4-Pivaloyloxy-4-phenylpiperidino)-ethyl]-1,4-benzodioxan hydrochloride

HRID 65965Notes

Reaction equation

HRID 65965 reaction equation
[OH:1][C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][CH:10]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[O:12][CH2:11]2)[CH2:4][CH2:3]1.C([Li])CCC.[C:31]([Cl:37])(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33].[Cl-].[NH4+]>O1CCCC1.CCCCCC.C(OCC)C>[ClH:37].[C:31]([O:1][C:2]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][CH:10]2[O:15][C:14]3[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=3[O:12][CH2:11]2)[CH2:6][CH2:7]1)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 62493Pivaloyl chlorideHCID 213319841-[2-(2,3-Dihydro-1,4-benzodioxin-2-yl)ethyl]-4-phenylpiperidin-4-olHCID 178418339Butyllithium

Product 1

HCID 213319702-[2-(4-Pivaloyloxy-4-phenylpiperidino)-ethyl]-1,4-benzodioxan hydrochloride

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

To the stirred solution of 4.0 g of 2-[2-(4-hydroxy-4-phenylpiperidino)-ethyl]-1,4-benzodioxan in 50 ml of anhydrous tetrahydrofuran is added 9.5 ml of 1.6 N n-butyl lithium in hexane at 0°. After warming the mixture up to room temperature, the solution of 1.5 ml of pivaloyl chloride in 10 ml of tetrahydrofuran is added while stirring and the whole is refluxed for 24 hours. After cooling 10 ml of saturated aqueous ammonium chloride are added, followed by 200 ml of diethyl ether. The organic layer is separated, washed with water, dried evaporated and the residue dissolved in isopropanol. The solution is made acidic with 6N ethanolic hydrogen chloride and the precipitate collected, to yield the 2-[2-(4-pivaloyloxy-4-phenylpiperidino)-ethyl]-1,4-benzodioxan hydrochloride melting at 195°-200° with decomposition.

Workup

  1. temperaturethe whole is refluxed for 24 hours
  2. additionare added
  3. customThe organic layer is separated
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. dissolutionthe residue dissolved in isopropanol
  8. customthe precipitate collected

Sources & evidence

ORD record
ord-fcca3f9e89e1400785501f050b40055a
Source dataset
uspto-grants-1978_12
Patent number
US04129655

Reaction notes

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