Fumaric Acid → HCID 131728949, compound

HRID 1478659Notes

Reaction equation

HRID 1478659 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-90dd68ecc65c4b2e81f91997bf3d8e6d
Source dataset
uspto-grants-2016_08
Patent number
US09403776B2

Reaction notes

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