Ammonium Chloride → HCID 68628529, compound

HRID 1750153Notes

Reaction equation

HRID 1750153 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([N+:27]([O-])=O)[CH:21]=2)[CH2:11][CH2:10]1.[Cl-].[NH4+]>CCO.O.[Fe]>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][CH2:17][CH2:18][O:19][C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[C:22]([CH:21]=2)[NH2:27])[CH2:13][CH2:14]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 66631925HCID 66631925, compound

Product 1

HCID 68628529HCID 68628529, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of intermediate 62 (180 mg, 0.41 mmol), Fe (70 mg, 1.23 mmol) and ammonium chloride (25 mg, 0.41 mmol) was dissolved in EtOH and H2O, and the solution was heated to reflux and stirred overnight. The solution was filtered, diluted with water, and then extracted with DCM. The combined organic layers were washed with saturated aq NaHCO3, brine, dried over anhydrous Na2SO4, and concentrated in vacuo to give 5-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-methylaniline (intermediate 63) (150 mg, 90%) as a yellow solid. HPLC: 99%, RT 3.197 min. MS (ESI) m/z 407.9 [M+H]+.

Workup

  1. temperatureto reflux
  2. filtrationThe solution was filtered
  3. additiondiluted with water
  4. extractionextracted with DCM
  5. washThe combined organic layers were washed with saturated aq NaHCO3, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e7a23b8023243b7b09ec26e6e65f842
Source dataset
uspto-grants-2015_10
Patent number
US09156822B2

Reaction notes

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