2-[4-(1-Methoxy-2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-piperazin-1-yl]-ethanol → 2-(4-(2-amino-1-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-yl)piperazin-1-yl)ethanol

HRID 2276305Notes

Reaction equation

HRID 2276305 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH2:11][CH:12]([N:14]3[CH2:19][CH2:18][N:17]([CH2:20][CH2:21][OH:22])[CH2:16][CH2:15]3)[CH2:13][C:7]=2[CH:6]=[CH:5][C:4]=1[N+:23]([O-])=O>C(O)C.[Pd]>[NH2:23][C:4]1[CH:5]=[CH:6][C:7]2[CH2:13][CH:12]([N:14]3[CH2:15][CH2:16][N:17]([CH2:20][CH2:21][OH:22])[CH2:18][CH2:19]3)[CH2:11][CH2:10][CH2:9][C:8]=2[C:3]=1[O:2][CH3:1]

Participants

4

Reactant 1

HCID 898152252-[4-(1-Methoxy-2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-piperazin-1-yl]-ethanol

Product 1

HCID 898135282-(4-(2-amino-1-methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-6-yl)piperazin-1-yl)ethanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-[4-(1-Methoxy-2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-piperazin-1-yl]-ethanol (19.0 g, 54.4 mmol) was split into two batches and dissolved in a total of Ethanol (232 mL). 10% Pd/C (1.74 g, 1.64 mmol) was divided in half and the reaction was hydrogenated for 3-4 hours at 50 psi. Each reaction mixture was filtered through celite to remove Pd. The filtrates were combined and then concentrated and the title compound isolated as a foamy solid (17.25 g, 99% yield). 1H-NMR (400 MHz, CDCl3) 6.76 (d, J=7.9 Hz, 1H), 6.53 (d, J=7.9 Hz, 1H), 3.72 (broad s, 3H), 3.71 (s, 3H), 3.64 (t, J=5.4 Hz, 2H), 3.26-3.20 (m, 1H), 2.84-2.72 (m, 5H), 2.62-2.56 (m, 8H), 2.42-2.35 (m, 2H), 2.40-2.37 (m, 1H), 1.81-1.74 (m, 1H), 1.70 (broad s, 1H), 1.41-1.33 (m, 1H). LC/MS (ESI+) m/z=320 (M+H)+

Workup

  1. filtrationEach reaction mixture was filtered through celite
  2. customto remove Pd
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3cdaa0898fe342bd94ff7e97648820a1
Source dataset
uspto-grants-2015_09
Patent number
US09132128B2

Reaction notes

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