Hydrochloric Acid → 3-((4-(4-Amino-2-chlorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

HRID 1878345Notes

Reaction equation

HRID 1878345 reaction equation
[C:1]([NH:5][C:6](=[O:32])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:31])[C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][C:22]=3[Cl:30])[CH2:16][CH2:15]2)[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].Cl>C(O)(C)C>[NH2:27][C:24]1[CH:25]=[CH:26][C:21]([C:20]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:32])[CH2:15][CH2:16]2)=[O:31])=[C:22]([Cl:30])[CH:23]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57917601N-tert-Butyl-3-((4-(2-chloro-4-nitrobenzoyl)piperazin-1-yl)methyl)benzamide

Product 1

HCID 579176443-((4-(4-Amino-2-chlorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamideYield 87.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-tert-Butyl-3-((4-(2-chloro-4-nitrobenzoyl)piperazin-1-yl)methyl)benzamide (1.9483 g, 4.2 mmol) was added to a suspension of reduced iron powder (2.3623 g, 42 mmol) and 1M hydrochloric acid (6 mL) in isopropanol. The reaction was stirred at room temperature for 2 hours. The reaction was concentrated under reduced pressure and the remaining residue was taken up in dichloromethane and washed with water. The organic phase was dried over magnesium sulphate and concentrated under vacuum to afford the title compound (1.57 g).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. washwashed with water
  3. dry with materialThe organic phase was dried over magnesium sulphate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-73ab9023160743b08d8157fee7ded299
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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