Hydrochloric Acid → HCID 67332145, compound

HRID 2061067Notes

Reaction equation

HRID 2061067 reaction equation
[CH3:1][C:2]([N+:14]([O-])=O)([CH3:13])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:12])[CH3:11])[CH2:6][CH2:5]1.[ClH:17]>CO.O>[ClH:17].[ClH:17].[NH2:14][C:2]([CH3:13])([CH3:1])[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10](=[O:12])[CH3:11])[CH2:6][CH2:5]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 60134450HCID 60134450, compound

Product 1

HCID 67332145HCID 67332145, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-(4-(2-methyl-2-nitropropyl)piperazin-1-yl)ethanone (7.2 g, 19.4 mmol) in a mixture of methanol and water (50:10 mL) was added to a steel pressure vessel equipped with a magnetic stir bar. The vessel was flushed with nitrogen while Raney nickel (50% aqueous suspension, 1.0 mL) was added in one portion. The vessel was sealed and pressurized with hydrogen (100 psi). The suspension was stirred for 5 min and the hydrogen released until the pressure was just above 0 psi. This was repeated once more and the vessel was finally pressurized to 500 psi. The reaction was stirred at room temperature for 17 h. The hydrogen was released and the suspension was filtered through Celite®. The solid was washed with small portions of water (5×40 mL) to give a colorless filtrate. The filtrate was brought to pH 2 with 6N HCl. The filtrate was concentrated in vacuo to a yellow oil. The oil was purified by Prep-LC utilizing a gradient of methanol and water with 0.05% acetic acid as a modifier. Fractions were pooled and concentrated to give foamy solid (6.91 g, 81%). 1H NMR (CDCl3, 400 MHz): δ 1.33 (s, 6H), 2.12 (s, 3H), 2.58 (s, 2H), 2.63-2.72 (dt, J=4.8, 4H), 3.57-3.60 (m, 4H). LRMS (ESI+) for C10H21N3O (199.1); Found: 200 (MH+).

Workup

  1. additionwas added to a steel pressure vessel
  2. customequipped with a magnetic stir bar
  3. customThe vessel was flushed with nitrogen while Raney nickel (50% aqueous suspension, 1.0 mL)
  4. additionwas added in one portion
  5. customThe vessel was sealed
  6. stirringThe reaction was stirred at room temperature for 17 h
  7. filtrationthe suspension was filtered through Celite®
  8. washThe solid was washed with small portions of water (5×40 mL)
  9. customto give a colorless filtrate
  10. concentrationThe filtrate was concentrated in vacuo to a yellow oil
  11. customThe oil was purified by Prep-LC
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-8c376bac3fca475cae3fd5a0d9de1faa
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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