HCID 14985988, compound → HCID 14985993, compound

HRID 1086852Notes

Reaction equation

HRID 1086852 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH:9]([CH:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[C:10]2=[O:13])=[CH:6][CH:5]=1)([O-])=O>C(O)C.O1CCCC1.[Ni]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH:9]([CH:14]3[CH2:15][CH2:16][N:17]([CH3:20])[CH2:18][CH2:19]3)[C:10]2=[O:13])=[CH:6][CH:5]=1

Participants

5

Reactant 1

HCID 14985988HCID 14985988, compound

Product 1

HCID 14985993HCID 14985993, compoundYield 105.9%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.86 g (0.0068 mol) of 6-nitro-2-(1-methyl-4-piperidyl)indan-1-one in 50 mL of absolute ethanol and 50 mL of tetrahydrofuran was hydrogenated at 10 psi over Raney nickel catalyst. After 2.5 hours, the catalyst was removed by filtration and the solvent was evaporated to give 1.76 g of crystalline 6-amino-2-(1-methyl-4-piperidyl)indan-1-one. To a solution of 1.04 g (0.00426 mol) of the 6-amino compound in 20 mL of methylene chloride and 3.4 g of pyridine was added 0.61 g (0.005 mol) of methanesulfonyl chloride. The mixture was stirred at room temperature for two hours, after which time it was poured onto water and made basic by the addition of a saturated sodium bicarbonate solution. The mixture was concentrated to dryness in vacuo, and the solid residue was extracted with two 50 mL portions of methylene chloride. Evaporation of the methylene chloride gave 1.56 g of 6-methanesulfonamido-2 -(1-methyl-4-piperidyl)indane-2-one as a colorless foam.

Workup

  1. customthe catalyst was removed by filtration
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-764b138c609b408e8abb0eb5b0db79d2
Source dataset
uspto-grants-1991_07
Patent number
US05032598

Reaction notes

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