Hydrochloric Acid → HCID 67980585, compound

HRID 2406240Notes

Reaction equation

HRID 2406240 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([N:16]2[CH2:25][CH2:24][C:19]3(OCC[O:20]3)[CH2:18][CH2:17]2)[CH3:15])=[CH:4][CH:3]=1.Cl>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH:14]([N:16]2[CH2:17][CH2:18][C:19](=[O:20])[CH2:24][CH2:25]2)[CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67054558HCID 67054558, compound

Product 1

HCID 67980585HCID 67980585, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
85 °C

Procedure

To a solution of 8-[1-(4′-Chloro-biphenyl-2-yl)-ethyl]-1,4-dioxa-8-aza-spiro[4.5]decane (3.1 g, 8.66 mmol) in dioxane-water (1:1 60 mL) is added HCl 37% (10.5 mL, 346 mmol). The reaction is then heated up to 85° C. for 26 hours. The solvent is then removed under vacuum and the aqueous phase is basified to pH=9 using sodium hydroxide 4N and then extracted with DCM. The organic layer is then washed with brine. The combined organic phase is then dried on MgSO4 and concentrated to afford 1-[1-(4′-Chloro-biphenyl-2-yl)-ethyl]-piperidin-4-one. The crude material is used without further purification. Found m/z ES+=314.2 (M+H); 1H NMR (400 MHz, CDCl3) δ 7.57 (1H, d, J=7.1 Hz), 7.32 (1H, t), 7.30 (2H, d, J=8.6 Hz), 7.22 (1H, t), 7.15 (2H, d, J=8.6 Hz), 7.09 (1H, d, J=6.1 Hz), 3.58 (1H, m), 2.63 (2H, m), 2.52 (2H, m), 2.25 (4H, t, J=6.1 Hz), 1.24 (3H, d, J=6.6 Hz).

Workup

  1. customThe solvent is then removed under vacuum
  2. extractionextracted with DCM
  3. washThe organic layer is then washed with brine
  4. customThe combined organic phase is then dried on MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a7cf9bc20c6b4c738374c7e06df82a0d
Source dataset
uspto-grants-2014_08
Patent number
US08809352B2

Reaction notes

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