Hydrochloric Acid → HCID 67542030, compound

HRID 1809792Notes

Reaction equation

HRID 1809792 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[C:19]3[O:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:18]=3[CH:17]=[CH:16][CH:15]=2)[C@@H:10]([O:27][CH2:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)[CH2:9]1)=O)(C)(C)C.[ClH:39]>>[ClH:39].[CH:17]1[C:18]2[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=3[O:20][C:19]=2[C:14]([C@H:11]2[CH2:12][CH2:13][NH:8][CH2:9][C@@H:10]2[O:27][CH2:28][C:29]2[CH:38]=[CH:37][C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=2)=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67542355HCID 67542355, compound

Product 1

HCID 67542030HCID 67542030, compound

Procedure

A mixture of (3R*,4R*)-4-dibenzofuran-4-yl-3-(naphthalen-2-ylmethoxy)-piperidine-1-carboxylic acid t-butyl ester (prepared analogously as described in Example 1; 191 mg, 0.38 mmol) and HCl (5 M in 2-propanol, 2 mL, 10 mmol) is stirred for 1 h at RT. The solvent is removed in vacuo and the residue purified by preparative HPLC (CH3CN/H2O). A saturated aqueous NaHCO3 solution is added to the combined pure fractions, CH3CN is evaporated in vacuo, and the remaining aqueous layer extracted twice with DCM. The combined organic phases are dried (Na2SO4) and evaporated. The resulting gum is treated with HCl (4M in 1,4-dioxane, 1 mL) and stirred for 30 min at RT. Evaporation of the solvent in vacuo yields (3R*,4R*)-4-dibenzofuran-4-yl-3-(naphthalen-2-ylmethoxy)-piperidine hydrochloride as a white solid: MS 408.6 [M+H]+; Rf 0.20 (DCM/MeOH 9:1).

Workup

  1. customprepared analogously
  2. customThe solvent is removed in vacuo
  3. customthe residue purified by preparative HPLC (CH3CN/H2O)
  4. additionA saturated aqueous NaHCO3 solution is added to the combined pure fractions, CH3CN
  5. customis evaporated in vacuo
  6. extractionthe remaining aqueous layer extracted twice with DCM
  7. dry with materialThe combined organic phases are dried (Na2SO4)
  8. customevaporated
  9. additionThe resulting gum is treated with HCl (4M in 1,4-dioxane, 1 mL)
  10. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-11b4e6e2c2fe4c30b0b444e231d03f42
Source dataset
uspto-grants-2013_01
Patent number
US08362040B2

Reaction notes

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