Hydrochloric Acid → HCID 9952958, compound

HRID 1369240Notes

Reaction equation

HRID 1369240 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][C@@H:20]([CH2:22][C:23]([O:25]CC)=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1.[OH-].[Na+].Cl>O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]2[CH2:21][C@@H:20]([CH2:22][C:23]([OH:25])=[O:24])[C:19]3[CH:28]=[CH:29][CH:30]=[CH:31][C:18]=3[CH2:17][C:16]=2[CH:32]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12071473HCID 12071473, compound

Product 1

HCID 9952958HCID 9952958, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of ethyl (S)-10,11-dihydro-3-[3-(pyridin-2-ylamino)-1-propyloxy]-5H-dibenzo[a,d]cycloheptene-10-acetate (29.20 g, 68 mmol) in dioxane (350 mL) was added aqueous 1.0 N NaOH (110 mL, 110 mmol). The cloudy reaction was stirred at 50° C. in an oil bath for 24 h, then the resulting homogeneous solution was neutralized with aqueous 1.0 N HCl (110 mL, 110 mmol). The solution was concentrated to near dryness by rotary evaporation to precipitate out the product. The supernatant was decanted off and the remaining gummy solid was dried under vacuum and redissolved in 1:1 methanol/CHCl3. The clear solution was then reconcentrated by rotary evaporation and thoroughly dried under vacuum. The remaining solid was triturated with a small volume of water, filtered and dried under vacuum to give the title compound (26.85 g, 94%) as an off-white powder: HPLC (Hamilton PRP-1®, 35% CH3CN/H2O containing 0.1% TFA) k′=2.88; 1H NMR (400 MHz, DMSO-d6) δ7.94 (dd, J=4.7, 1.6 Hz, 1H), 7.38 (m, 1 H), 7.18 (d, J=7.3 Hz, 1H), 7.14 (d, J=3.9 Hz, 2H), 7.08 (m, 1H), 6.97 (d, J=8.4 Hz, 1H),6.83 (d, J=8.6 Hz, 1H), 6.78 (br s, 1H), 6.68 (dd, J=8.3. 2.6 Hz, 1H), 6.50 (d, J=8.3 Hz, 1H), 6.47 (dd, 1H), 4.20 (d, J=14.6 Hz, 1H), 4.00 (t, 2 H), 3.88 (d, J=14.6 Hz, 1 H), 3.67 (m, 1H), 3.37 (m, 1 H), 3.20 (dd, J=1.2, 4.4 Hz, 1H), 2.83 (dd, J=15.2, 10.1 Hz, 1H), 2.60 (dd, J=15.9, 5.3 Hz, 1H), 2.50 (dd, 1H), 1.95 (m, 2 H); MS (ES) m/e 403.3 (M+H)+ Anal. Calcd for C25H26N2O3.H2O: C, 71.41; H, 6.71; N, 6.66. Found: C, 71.21; H, 6.53: N, 6.54.

Workup

  1. customThe cloudy reaction
  2. concentrationThe solution was concentrated
  3. customby rotary evaporation
  4. customto precipitate out the product
  5. customThe supernatant was decanted off
  6. customthe remaining gummy solid was dried under vacuum
  7. dissolutionredissolved in 1:1 methanol/CHCl3
  8. customThe clear solution was then reconcentrated by rotary evaporation
  9. customthoroughly dried under vacuum
  10. customThe remaining solid was triturated with a small volume of water
  11. filtrationfiltered
  12. customdried under vacuum

Sources & evidence

ORD record
ord-f063434386bb4dc1931d54801156282e
Source dataset
uspto-grants-2003_06
Patent number
US06576643B2

Reaction notes

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