HCID 21102222, compound → HCID 21102117, compound

HRID 2355947Notes

Reaction equation

HRID 2355947 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=O)[C:16]2[C:21]([N+:22]([O-])=O)=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:25])[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>[NH2:22][C:21]1[CH:20]=[CH:19][CH:18]=[C:17]([Cl:25])[C:16]=1[CH2:15][NH:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9][CH2:10]1

Participants

4

Reactant 2

HCID 21102222HCID 21102222, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21102117HCID 21102117, compound

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-chloro-6-nitro-benzamide (1.67 g, 4.47 mmol) and lithium aluminium hydride (0.51 g, 13.43 mmol) were combined. To this was added anhydrous 1,4-dioxane (15 mL). The mixture was slowly brought to reflux and stirred 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
  3. customexcess lithium aluminium hydride destroyed by dropwise addition of methanol
  4. additionfollowed by careful addition of 20% potassium hydroxide
  5. filtrationThe aluminum salts were filtered
  6. concentrationthe filtrate concentrated
  7. customas is for the next reaction

Sources & evidence

ORD record
ord-c1aa4f0223364b80bbe1afe8af0e8a70
Source dataset
uspto-grants-2010_07
Patent number
US07754732B2

Reaction notes

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