2-nitro-N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-Pyran-4-yl}methyl)aniline → N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)benzene-1,2-diamine

HRID 272984Notes

Reaction equation

HRID 272984 reaction equation
[N+:1]([C:4]1[CH:32]=[CH:31][CH:30]=[CH:29][C:5]=1[NH:6][CH2:7][C:8]1([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[CH:16][CH:15]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([O-])=O>C(O)C.[Pd]>[N:24]1([CH2:23][CH2:22][CH2:21][O:20][C:17]2[CH:16]=[CH:15][C:14]([C:8]3([CH2:7][NH:6][C:5]4[C:4]([NH2:1])=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH2:9][CH2:10][O:11][CH2:12][CH2:13]3)=[CH:19][CH:18]=2)[CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

4

Reactant 1

HCID 685760832-nitro-N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-Pyran-4-yl}methyl)aniline

Product 1

HCID 68576071N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-nitro-N-({4-[4-(3-pyrrolidin-1-ylpropoxy)phenyl]tetrahydro-2H-pyran-4-yl}methyl)aniline (570 mg, 1.3 mmol) in ethanol (40 mL) was hydrogenated for 5 hours at room temperature at 50 psi in the presence of 10% Pd/C (60 mg, 10% w/w). The reaction mixture was filtered over Arbocel® and rinsed with ethanol. The filtrate was concentrated in vacuo to give the title compound as a gum, used without further purification (500 mg, 94%). HRMS ESI+ m/z 410.2791 [MH]+.

Workup

  1. filtrationThe reaction mixture was filtered over Arbocel®
  2. washrinsed with ethanol
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-c449f71638c8455b9d8ee36f3c0376c1
Source dataset
uspto-grants-2008_11
Patent number
US07456164B2

Reaction notes

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