Acetic Acid → HCID 178418702, compound

HRID 11524

Reaction equation

HRID 11524 reaction equation
[N+:1]([C:4]1[CH:16]=[CH:15][C:7]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:5]=1)([O-])=O.Cl.[OH-:18].[Na+].N1([CH2:26][NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)CCCCC1.[C:34](O)(=O)[CH3:35]>O>[N:9]1([CH2:8][C:7]2[CH:15]=[CH:16][C:4]([NH:1][CH:34]=[C:35]3[C:29]4[C:28](=[CH:33][CH:32]=[CH:31][CH:30]=4)[NH:27][C:26]3=[O:18])=[CH:5][CH:6]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 7835411-(4-Nitrobenzyl)piperidineHCID 21974891Piperidin-1-ylmethyl-phenylamine

Product 1

HCID 178418702HCID 178418702, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(4-Nitro-benzyl)-piperidine (0.5052 gms.) is suspended in 25 mL of a 1:1 (v:v) solution of acetic acid and water. The suspension is then treated with 45 mL of an ˜10 wt. % solution of TiCl3 in 20–30 wt. % HCl, dropwise. Over the course of the addition a color change from colorless to purple to black ensues. The reaction mixture is immersed in a 60° C. oil bath overnight following the addition of TiCl3. The reaction mixture is then cooled to room temperature and made basic with the addition of a 10% aqueous solution of NaOH. The basic reaction mixture is extracted with chloroform, and the organic layer is dried over anhydrous sodium sulfate. Following evaporation of the solvent the organic layer yields 0.333 gms. of piperidin-1-ylmethyl-phenylamine.

Workup

  1. additionOver the course of the addition a color change from colorless to purple to black ensues
  2. customis immersed in a 60° C.
  3. customovernight
  4. customThe basic reaction mixture
  5. extractionis extracted with chloroform
  6. dry with materialthe organic layer is dried over anhydrous sodium sulfate
  7. customevaporation of the solvent the organic layer
  8. customyields 0.333 gms

Sources & evidence

ORD record
ord-1439421f0cf641689aef96f1a9448bf3
Source dataset
uspto-grants-2006_08
Patent number
US07098236B2

Linked notes

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