Hydrochloric Acid → HCID 68294367, compound

HRID 2279562Notes

Reaction equation

HRID 2279562 reaction equation
[C:1]([C:3]1([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1)#N.Cl.[OH-:25].[Na+].CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[OH2:42]>O1CCOCC1>[C:12]([O:11][C:9]([N:6]1[CH2:7][CH2:8][C:3]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([Cl:23])[CH:17]=2)([C:1]([OH:42])=[O:25])[CH2:4][CH2:5]1)=[O:10])([CH3:14])([CH3:15])[CH3:13]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 90495Di-tert-butyl dicarbonateHCID 49760263tert-Butyl 4-cyano-4-(3,4-dichlorophenyl)piperidine-1-carboxylate

Product 1

HCID 68294367HCID 68294367, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 356 (4.54 g, 12.78 mmol) and concentrated HCl (106.5 mL, 1278 mmol) was heated to reflux and stirred over the weekend. The reaction mixture was then cooled to RT, transferred to separatory funnel, and washed with Et2O (1×200 mL). The aqueous layer was concentrated in a rotovap under high vacuum. The resulting solids were dissolved in 10% NaOH (20.45 g, 51.12 mmol). To the solution was added dioxane (30 mL) followed by Boc2O (2.929 g, 13.42 mmol). After stirring overnight, the reaction was diluted with H2O (100 mL) and washed with ether (1×100 mL). The aqueous layer was acidified with solid KHSO4 and then extracted with DCM (200 mL). The combined extracts were dried (MgSO4), filtered, concentrated and dried under high vacuum to afford 1.98 g (41%) of 1-(tert-butoxycarbonyl)-4-(3,4-dichlorophenyl)piperidine-4-carboxylic acid (358) as a white foam.

Workup

  1. temperatureto reflux
  2. customtransferred to separatory funnel
  3. washwashed with Et2O (1×200 mL)
  4. concentrationThe aqueous layer was concentrated in a rotovap under high vacuum
  5. stirringAfter stirring overnight
  6. washwashed with ether (1×100 mL)
  7. extractionextracted with DCM (200 mL)
  8. dry with materialThe combined extracts were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customdried under high vacuum

Sources & evidence

ORD record
ord-7cfba998ecea47a3972c8a073ccc2597
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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