1,4-Dioxane → 4-allyl-N-(3-chlorophenyl)piperidine-4-carboxamide

HRID 216029Notes

Reaction equation

HRID 216029 reaction equation
[CH2:1]([C:4]1([C:17](=[O:26])[NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)[CH2:9][CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5]1)[CH:2]=[CH2:3].O1CCOCC1>CO>[CH2:1]([C:4]1([C:17]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[O:26])[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 67036827Tert-butyl 4-allyl-4-(3-chlorophenylcarbamoyl)piperidine-1-carboxylate

Product 1

HCID 689911124-allyl-N-(3-chlorophenyl)piperidine-4-carboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 4-allyl-4-(3-chlorophenylcarbamoyl)piperidine-1-carboxylate from step A (0.172 g, 0.453 mmol) in MeOH (10 mL) was added 4 MHCl in dioxane (0.340 mL, 1.36 mmol). The reaction was heated at 50° C. for 30 min, and then concentrated under vacuum, re-dissolved in MeOH and re-concentrated twice to give the title compound as the hydrochloride salt. MS (ES+) [M+H]+=279.

Workup

  1. concentrationconcentrated under vacuum
  2. dissolutionre-dissolved in MeOH
  3. concentrationre-concentrated twice

Sources & evidence

ORD record
ord-6498dcf92aa943d1b591ff9b658bcf7e
Source dataset
uspto-grants-2012_06
Patent number
US08193202B2

Reaction notes

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