Ammonia → HCID 22228384, compound

HRID 1744260Notes

Reaction equation

HRID 1744260 reaction equation
CO[N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([N:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.N.[H][H]>[Pd].CO>[N:13]1([C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[CH:4]([NH2:3])[CH2:5][CH2:6]3)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 86015016HCID 86015016, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22228384HCID 22228384, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Piperidin-1-ylindan-1-one O-methyloxime (2.95 g, 12 mmol), 10% palladium on carbon (1.45 g), and 20% ammonia in methanol (80 ml), were placed in a Parr apparatus which was charged with hydrogen to 60 psi. The mixture was shaken for 1 hour at ambient temperature and filtered. The filtrate was removed under vacuum to provide the title compound which was used without further purification. 1H NMR (CDCl3) δ 1.53–1.60 (m, 2H), 1.65–1.79 (m, 4H), 2.42–2.53 (m, 1H), 2.69–2.81 (m, 1H), 2.86–2.96 (m, 1H), 3.12 (t, 4H), 4.31 (t, 1H), 6.82 (m, 2H), 7.20 (d, 1H); MS (DCI) 217 (M+H)+.

Workup

  1. filtrationfiltered
  2. customThe filtrate was removed under vacuum

Sources & evidence

ORD record
ord-789b24e67400439d97edd99af1800895
Source dataset
uspto-grants-2006_03
Patent number
US07015233B2

Reaction notes

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