Fumaric Acid → HCID 131728950, compound

HRID 1478662Notes

Reaction equation

HRID 1478662 reaction equation
[CH3:1][O:2][C:3]1[C:13]2[CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][CH2:10][N:9]([CH3:20])[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25]>C(O)C.CO>[C:21]([OH:28])(=[O:27])/[CH:22]=[CH:23]/[C:24]([OH:26])=[O:25].[CH3:1][O:2][C:3]1[C:13]2[CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][CH2:10][N:9]([CH3:20])[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 66964436HCID 66964436, compound

Product 1

HCID 131728950HCID 131728950, compoundYield 52.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 6-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine from step B (334 mg, 1.25 mmol) in ethanol (5 mL) was added fumaric acid (145 mg, 1.25 mmol) in methanol (3 mL). The solvent was removed under reduced pressure. The residue was triturated with ethyl acetate and diethyl ether. The resulting precipitate was collected by filtration, washed with diethyl ether, and dried at 50° C. under vacuum to provide (+/−)-6-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt (250 mg, 67%, 96.6% AUC HPLC) as an off-white solid: mp 154-156° C.; 1H NMR (CD3OD, 500 MHz) δ 7.41-7.37 (m, 1H), 7.30 (t, J=7.6 Hz, 2H), 7.23-7.17 (m, 2H), 7.05-7.03 (m, 3H), 6.68 (s, 2H), 5.25-5.24 (m, 1H), 4.29-4.27 (m, 1H), 4.11 (d, J=13.9 Hz, 1H), 3.79 (s, 3H), 3.44-3.39 (m, 1H), 3.33-3.32 (m, 1H), 2.81 (s, 3H), 2.68-2.67 (m, 1H), 2.46-2.41 (m, 1H). ESI MS m/z=268 [C18H21NO+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was triturated with ethyl acetate and diethyl ether
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with diethyl ether
  5. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-8782659a62f5437baf41126bce505bd2
Source dataset
uspto-grants-2016_08
Patent number
US09403776B2

Reaction notes

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