HCID 59770003, compound → HCID 59769952, compound

HRID 2218659Notes

Reaction equation

HRID 2218659 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1>C(O)C.[Pd]>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[CH:6]([CH2:16][C:17]3[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 59770003HCID 59770003, compound

Product 1

HCID 59769952HCID 59769952, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolve N-[3-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide (100 mg, 0.265) in ethanol (25 mL) and add 10% Pd/C (56 mg). Pressurize to 60 psi with H2 and shake overnight at room temperature. Filter reaction through a pad of Celite and concentrate filtrate to 54 mg (54%) of white foam, mp 149.0° C. 1H NMR (CDCl3) δ 2.70 (s, 3H), 2.98 (br q, 2H), 3.28 (d, 2H), 3.40 (br q, 2H), 4.11 (br s, 1H), 6.16 (s, 1H), 6.58 (s, 1H), 6.82-7.20 (m, 11H); MS (S) 395 (M+Na), 376 (M−H). HPLC shows 94% purity.

Workup

  1. filtrationFilter
  2. customreaction through a pad of Celite
  3. concentrationconcentrate filtrate to 54 mg (54%) of white foam, mp 149.0° C

Sources & evidence

ORD record
ord-ecce8ad093bb47bd84555afd2d905f37
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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