N-(1-benzylpiperidin-4-yl)-2-(2-nitrophenyl)acetamide → N-(2-aminophenethyl)-1-benzylpiperidin-4-amine

HRID 2250247Notes

Reaction equation

HRID 2250247 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=O)[CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[N+:23]([O-])=O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCOCC1>[NH2:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[CH2:16][CH2:15][NH:14][CH:11]1[CH2:10][CH2:9][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:13][CH2:12]1

Participants

4

Reactant 2

HCID 2225138N-(1-benzylpiperidin-4-yl)-2-(2-nitrophenyl)acetamideHCID 21226445Aluminium lithium hydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Into a flame dried flask, N-(1-benzyl-piperidin-4-yl)-2-(2-nitro-phenyl)-acetamide (3.2 g, 9.06 mmol) and lithium aluminium hydride (1.0 g, 18.12 mmol) were combined. 1,4-Dioxane (15 mL) was added and the mixture slowly brought to reflux over 1 h and stirred at reflux for 16 h. The reaction mixture was cooled to 0° C. and excess lithium aluminium hydride destroyed by dropwise addition of methanol, followed by careful addition of 20% potassium hydroxide. The aluminum salts were filtered, the filtrate concentrated and used as is for the next reaction.

Workup

  1. customInto a flame dried flask
  2. temperatureto reflux over 1 h
  3. temperatureat reflux for 16 h
  4. customexcess lithium aluminium hydride destroyed by dropwise addition of methanol
  5. additionfollowed by careful addition of 20% potassium hydroxide
  6. filtrationThe aluminum salts were filtered
  7. concentrationthe filtrate concentrated
  8. customas is for the next reaction

Sources & evidence

ORD record
ord-ed8966aa60ce4543b7d2e78e722b70a5
Source dataset
uspto-grants-2008_01
Patent number
US07314883B2

Reaction notes

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