HCID 23372181, compound → HCID 15388862, compound

HRID 1900247Notes

Reaction equation

HRID 1900247 reaction equation
[CH3:1][NH:2][CH2:3][CH:4]([CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][O:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[CH2:5][CH:6]=[CH2:7]>C(O)C.[Pd]>[CH3:1][NH:2][CH2:3][CH:4]([CH:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[CH2:12][O:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[CH2:5][CH2:6][CH3:7]

Participants

4

Reactant 1

HCID 23372181HCID 23372181, compound

Product 1

HCID 15388862HCID 15388862, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Dissolved N-methyl-2-[6,11-dihydro-dibenzo[b,e]oxepin-11-yl]-pent-4-en-1-amine (0.50 g, 2.08 mmol) in 15 mL of absolute ethanol. Added 10 mg of 10% palladium on carbon catalyst, and stirred under atmospheric hydrogen balloon for 16 hours. Filtered through Celite, and washed with ethanol. Evaporated filtrate. Purified crude product by flash chromatography on silica gel eluting with 5% MeOH--CH2Cl2. Combined appropriate fractions, and evaporated to give 0.43 g (86% yield) of N-methyl-2-[6,11-dihydro-dibenzo[b,e]oxepin-11-yl]-pentanamine. Dissolved free base in ethyl acetate, and added one equivalent of maleic acid dissolved in absolute ethanol. Evaporated to foamy glass.

Workup

  1. filtrationFiltered through Celite
  2. washwashed with ethanol
  3. customPurified crude product by flash chromatography on silica gel eluting with 5% MeOH
  4. customevaporated

Sources & evidence

ORD record
ord-fe3e6131ca304caab241b131de9d9052
Source dataset
uspto-grants-1996_11
Patent number
US05574173

Reaction notes

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