N-(2-nitrophenethyl)-1-benzylpiperidin-4-amine → N-(2-aminophenethyl)-1-benzylpiperidin-4-amine

HRID 2378932Notes

Reaction equation

HRID 2378932 reaction equation
[N+:1]([C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1)([O-])=O.[H][H]>CO.[Pt](=O)=O>[NH2:1][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][CH2:7][NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 16202487N-(2-nitrophenethyl)-1-benzylpiperidin-4-amineHCID 178418361HCID 178418361, compound

Product 1

HCID 21102095N-(2-aminophenethyl)-1-benzylpiperidin-4-amine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 887MethanolSolvent

Procedure

N-(2-Nitrophenethyl)-1-benzylpiperidin-4-amine (1.98 g, 5.83 mmol) was dissolved in methanol (60 mL). Platinum(IV) oxide (55 mg, 0.242 mmol) was added to the mixture. Reaction vessel was placed on a Parr apparatus and charged with 50 psi of hydrogen gas. Reaction shook at room temperature for 75 minutes. Mixture was removed from the apparatus and then filtered over celite. Filtrate was concentrated to dryness. Title compound was obtained as brown oil in quantitative yield. MS (M+H)+=310.4.

Workup

  1. customReaction vessel
  2. customReaction
  3. customMixture was removed from the apparatus
  4. filtrationfiltered over celite
  5. concentrationFiltrate was concentrated to dryness

Sources & evidence

ORD record
ord-e6f0b6eed8fb466199e73cbcb048c494
Source dataset
uspto-grants-2008_12
Patent number
US07470680B2

Reaction notes

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