Fumaric Acid → HCID 131728949, compound

HRID 2421469Notes

Reaction equation

HRID 2421469 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][N:9]([CH3:19])[CH2:8][C:7]=2[CH:20]=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[CH:4]=[CH:5][C:6]2[CH:12]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:11][CH2:10][N:9]([CH3:19])[CH2:8][C:7]=2[CH:20]=1

Participants

5

Reactant 2

HCID 444972Fumaric AcidHCID 66964783HCID 66964783, compound

Product 1

HCID 131728949HCID 131728949, compoundYield 67.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a solution of 8-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine from step B (260 mg, 0.97 mmol) in ethanol (4 mL) was added fumaric acid (123 mg, 0.97 mmol) in methanol (2 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 (+/−)-8-methoxy-2-methyl-5-phenyl-2,3,4,5-tetrahydro-1H-benzo[c]azepine, fumarate salt (250 mg, 67%, >99% AUC HPLC) as an off-white solid: mp 171-173° C.; 1H NMR (CD3OD, 500 MHz) δ 7.38 (t, J=7.5 Hz, 2H), 7.29 (t, J=7.4 Hz, 1H), 7.18 (d, J=7.5 Hz, 2H), 7.02 (d, J=2.7 Hz, 1H), 6.86-6.78 (m, 2H), 6.67 (s, 2H), 4.50 (dd, J=8.9, 1.9 Hz, 2H), 4.25 (d, J=13.9 Hz, 1H), 3.80 (s, 3H), 3.52-3.51 (m, 2H), 2.85 (s, 3H), 2.57-2.56 (m, 1H), 2.40-2.36 (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-613d193b87ea459687f54819c87815c0
Source dataset
uspto-grants-2011_06
Patent number
US07956050B2

Reaction notes

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