Fumaric Acid → HCID 131728950, compound

HRID 2421472Notes

Reaction equation

HRID 2421472 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-7af1309ce22a4a3faf9ac6d19087574e
Source dataset
uspto-grants-2011_06
Patent number
US07956050B2

Reaction notes

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