Hydrochloric Acid → 2-amino-5-methylthio-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

HRID 362913Notes

Reaction equation

HRID 362913 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([N+:32]([O-])=O)=[C:7]([CH:31]=1)[C:8]([NH:10][CH2:11][CH:12]1[CH2:17][CH2:16][N:15]([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:14][CH2:13]1)=[O:9].Cl.O>[Fe].CCO>[NH2:32][C:6]1[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:31][C:7]=1[C:8]([NH:10][CH2:11][CH:12]1[CH2:13][CH2:14][N:15]([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:16][CH2:17]1)=[O:9]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 675968055-methylthio-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Product 1

HCID 675947392-amino-5-methylthio-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

Step 2): A mixture of 5-methylthio-2-nitro-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide (500 mg, 1.05 mmol), Fe powder (587 mg, 1.05 mmol), conc. HCl (0.05 ml), H2O (8 ml) and EtOH (35 ml) was refluxed overnight. The insoluble precipitates were filtered off and then the filtrate was evaporated to give 2-amino-5-methylthio-N-[(1-diphenylmethylpiperidin-4-yl)methyl]benzamide as colorless powder, 450 mg (96%): mp 156°-157° C.

Workup

  1. temperaturewas refluxed overnight
  2. customThe insoluble precipitates
  3. filtrationwere filtered off
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-5d559bfd3de84d1fb42389fff5bea64a
Source dataset
uspto-grants-1999_02
Patent number
US05872115

Reaction notes

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