(2,2-Difluoro-ethyl)-(2-nitro-6,7,8,9-tetrahydro-5h-benzocyclohepten-7-yl)-amine → N*7*-(2,2-Difluoro-ethyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamine

HRID 1040990Notes

Reaction equation

HRID 1040990 reaction equation
[F:1][CH:2]([F:19])[CH2:3][NH:4][CH:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1.[H][H]>[Pd].CO>[F:1][CH:2]([F:19])[CH2:3][NH:4][CH:5]1[CH2:11][CH2:10][C:9]2[CH:12]=[C:13]([NH2:16])[CH:14]=[CH:15][C:8]=2[CH2:7][CH2:6]1

Participants

5

Reactant 2

HCID 87330341(2,2-Difluoro-ethyl)-(2-nitro-6,7,8,9-tetrahydro-5h-benzocyclohepten-7-yl)-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 131729566N*7*-(2,2-Difluoro-ethyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamineYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2,2-Difluoro-ethyl)-(2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-yl)-amine (625 mg, 2.31 mmol) was charged to 30 ml methanol and 200-400 mg 10% palladium on carbon was added. The suspension was hydrogenated at 30 psi hydrogen for 2.5 hours and followed by NMR. The reaction was filtered through a ¼″ pad of celite and the pad washed with 4×10 ml portions of methanol. The resulting solution was clarified through a 45 micron frit to yield a yellow solution that was evaporated to yield N*7*-(2,2-Difluoro-ethyl)-6,7,8,9-tetrahydro-5H-benzocycloheptene-2,7-diamine (492 mg, 89% yield) as a white solid. 1H-NMR (CDCl3) δ 6.88 (m, 1H), 6.44 (m, 2H), 5.82 (m, 1H), 3.00 (m, 2H), 2.66 (m, 5H), 2.04 (m, 2H), 1.27 (m, 2H). LC/MS (ESI+)=241 (M+H).

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered through a ¼″ pad of celite
  3. washthe pad washed with 4×10 ml portions of methanol
  4. customto yield a yellow solution that
  5. customwas evaporated

Sources & evidence

ORD record
ord-9dfb8dc97b59405c83bf6bffda89d6d3
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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