3-Nitro-9-(2-pyrrolidin-1-yl-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene → 9-(2-Pyrrolidin-1-yl-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine

HRID 1688033Notes

Reaction equation

HRID 1688033 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][C:7]2[N:8]([CH2:13][CH2:14][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-])=O>[Pd].C(O)C>[N:15]1([CH2:14][CH2:13][N:8]2[C:7]3[CH:20]=[CH:21][C:4]([NH2:1])=[CH:5][C:6]=3[O:12][CH2:11][CH2:10][CH2:9]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 1

HCID 672645583-Nitro-9-(2-pyrrolidin-1-yl-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene

Product 1

HCID 672643719-(2-Pyrrolidin-1-yl-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

10% Palladium on Carbon (50% Wet) (174 mg) and 3-Nitro-9-(2-pyrrolidin-1-yl-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (270 mg, 0.93 mmol) in Ethanol (15 mL) was shaken under an atmosphere of Hydrogen (40 psi) overnight. The mixture was filtered over Celite, washing with 60 mL ethanol. After conc., 9-(2-Pyrrolidin-1-yl-ethyl)-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-3-ylamine was obtained as an oil (224 mg, 92%). 1H-NMR (CDCl3): 6.80 (d, 1H, J=8.0 Hz), 6.34 (m, 2H), 4.05 (m, 2H), 3.44 (br s, 2H), 3.27 (m, 2H), 3.14 (t, 2H, J=5.6 Hz), 2.65 (t, 2H, J=7.2 Hz), 2.56 (m, 4H), 1.98 (m, 2H), 1.78 (m, 4H).

Workup

  1. filtrationThe mixture was filtered over Celite
  2. washwashing with 60 mL ethanol

Sources & evidence

ORD record
ord-76faea6340f64959b0b1aab0f743dcd4
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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