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

HRID 2419109
Notes
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Reaction equation

HRID 2419109 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 3283
Diethyl Ether
Solvent
HCID 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-6c5e45ea3cd7444e86eee7e282852346
Source dataset
uspto-grants-1978_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04104396

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes