Ethyl Acetate → (2s,3r)-n-(2-((3-Pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide d-mandelate salt

HRID 1013143Notes

Reaction equation

HRID 1013143 reaction equation
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C@H:19]2[C@H:24]([NH:25][C:26]([C:28]3[O:29][C:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=4[CH:32]=3)=[O:27])[CH:23]3[CH2:37][CH2:38][N:20]2[CH2:21][CH2:22]3)[CH:13]=1.C(OCC)(=O)C>C(O)C>[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][C@H:19]2[C@H:24]([NH:25][C:26]([C:28]3[O:29][C:30]4[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=4[CH:32]=3)=[O:27])[CH:23]3[CH2:37][CH2:38][N:20]2[CH2:21][CH2:22]3)[CH:13]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11914(-)-Mandelic acidHCID 25147644Bradanicline

Product 1

HCID 131729023(2s,3r)-n-(2-((3-Pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide d-mandelate saltYield 62.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

D-Mandelic acid (52.6 mg, 0.346 mmol) was added to a solution of (2S,3R)—N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide (125 mg, 0.346 mmol) in hot ethanol (1 mL). Dilution with ethyl acetate (4 mL) and cooling failed to produce a precipitate. The volatiles were removed by rotary evaporation, and the residue (white foam) was dissolved in hot isopropanol (0.5 mL). Cooling to 5° C. produced white crystals which were collected by suction filtration. Vacuum oven drying (18 h at 45° C.) gave 111 mg (62.4% yield) of light beige solid, mp 188.5-193° C. 1H NMR (300 MHz, D2O) δ 8.33 (s, 1H), 7.83 (s, 1H), 7.67 (d, 1H), 7.60 (d, 1H), 7.27 (m, 8H, includes mandelic acid), 7.12 (s, 1H), 7.01 (m, 1H), 4.85 (s, 1H, mandelic acid), 4.10 (d, 1H), 3.75 (m, 1H), 3.48 (m, 2H), 3.00-3.40 (m, 4H), 1.75-2.15 (m, 5H).

Workup

  1. customto produce a precipitate
  2. customThe volatiles were removed by rotary evaporation
  3. dissolutionthe residue (white foam) was dissolved in hot isopropanol (0.5 mL)
  4. customproduced white crystals which
  5. filtrationwere collected by suction filtration
  6. customVacuum oven drying (18 h at 45° C.)
  7. customgave 111 mg (62.4% yield) of light beige solid, mp 188.5-193° C

Sources & evidence

ORD record
ord-11c0af1546e74d0bb914a67106d9a15d
Source dataset
uspto-grants-2011_07
Patent number
US07981906B2

Reaction notes

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