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Ammonium Chloride → 1,1-Dimethylethyl (2R,6S)-4-[(4-aminophenyl)methyl]-2,6-dimethyl-1-piperazinecarboxylate

HRID 534723
Notes
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Reaction equation

HRID 534723 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:5][C@H:4]([CH3:18])[N:3]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[Cl-].[NH4+]>CO.O.[Fe]>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:6]2[CH2:5][C@H:4]([CH3:18])[N:3]([C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[C@H:2]([CH3:1])[CH2:7]2)=[CH:10][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 592622131,1-Dimethylethyl (2R,6S)-2,6-dimethyl-4-[(4-nitrophenyl)methyl]-1-piperazinecarboxylate

Product 1

HCID 592622361,1-Dimethylethyl (2R,6S)-4-[(4-aminophenyl)methyl]-2,6-dimethyl-1-piperazinecarboxylateYield 70.4%

Reagents, catalysts & solvents 3

HCID 23925IronCatalyst
HCID 887
Methanol
Solvent
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,1-dimethylethyl (2R,6S)-2,6-dimethyl-4-[(4-nitrophenyl)methyl]-1-piperazinecarboxylate (D7) (2.62 g, 7.53 mmol) in MeOH (25 mL) and water (25 mL) heated to 80° C. was added iron powder (1.26 g, 22.54 mmol) and ammonium chloride (2.01 g, 37.58 mmol). The reaction was stirred vigorously at 80° C. for 1.5 h and then the iron residues removed by filtration through Celite®. The filtrate was concentrated and the residue partitioned between DCM and water. The aqueous layer was further extracted with DCM (×2) and the combined organics were dried and concentrated to give the crude product as a yellow foam (2.01 g). Column chromatography eluting with 0-100% Et2O/petroleum ether gave the title compound (1.694 g). δH (CDCl3, 400 MHz) 7.12 (2H, d), 6.64 (2H, d), 4.05 (2H, m), 3.64 (2H, br s), 3.36 (2H, s), 2.59 (2h, d), 2.06 (2H, dd), 1.46 (9H, s), 1.27 (6H, d). MS (ES): MH+ 320.3, MNa+ 342.3.

Workup

  1. customthe iron residues removed by filtration through Celite®
  2. concentrationThe filtrate was concentrated
  3. customthe residue partitioned between DCM and water
  4. extractionThe aqueous layer was further extracted with DCM (×2)
  5. customthe combined organics were dried
  6. concentrationconcentrated
  7. customto give the crude product as a yellow foam (2.01 g)
  8. washColumn chromatography eluting with 0-100% Et2O/petroleum ether

Sources & evidence

ORD record
ord-242f28a99bc8428594dc4404e83b2dfe
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08853218B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes