HCID 67264695, compound → 1-(2-Amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone

HRID 1041679Notes

Reaction equation

HRID 1041679 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:13][CH2:12][CH2:11][CH2:10][N:9]([C:14](=[O:21])[CH2:15][N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[C:8]=2[CH:22]=1)([O-])=O>[Pd].O1CCCC1.C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[O:13][CH2:12][CH2:11][CH2:10][N:9]([C:14](=[O:21])[CH2:15][N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)[C:8]=2[CH:22]=1

Participants

5

Reactant 1

HCID 67264695HCID 67264695, compound

Product 1

HCID 672649001-(2-Amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-(2-Nitro-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone (0.402 g, 1.32 mmol) and 10% Palladium on Carbon (50% Wet) (0.1 g) in Tetrahydrofuran (10 mL; EMD) and Ethanol (10 mL) was shaken under an atmosphere of Hydrogen (25 psi) overnight. Filtration and washing with ethanol (50 mL) followed by conc. afforded 1-(2-Amino-7,8-dihydro-6H-5-oxa-9-aza-benzocyclohepten-9-yl)-2-pyrrolidin-1-yl-ethanone as an oil in quantitative yield. 1H-NMR (CDCl3): 6.93 (d, 1H, J=8 Hz), 6.58 (d, 1H, J=8 Hz), 6.57 (s, 1H), 4.77 (m, 1H), 4.36 (m, 1H), 4.01 (br s, 2H), 3.76 (m, 1H), 3.56 (m, 1H), 3.10 (m, 1H), 2.94 (m, 4H), 2.71 (m, 1H), 2.25 (m, 1H), 1.91 (m, 4H), 1.71 (m, 1H), 0.86 (m, 1H).

Workup

  1. filtrationFiltration
  2. washwashing with ethanol (50 mL)

Sources & evidence

ORD record
ord-55be230c29994c6b8e3362d0f5f95c8b
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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