Hydrochloric Acid → HCID 66938556, compound

HRID 1716897Notes

Reaction equation

HRID 1716897 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([N+:17]([O-])=O)[CH:11]=2)[CH2:4][CH2:3]1.CO.Cl.[OH-].[Na+]>C(OCC)(=O)C.[Fe]>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([NH:8][CH2:9][C:10]2[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([NH2:17])[CH:11]=2)[CH2:6][CH2:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 66938698HCID 66938698, compound

Product 1

HCID 66938556HCID 66938556, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Combine 1-methyl-4-(N-(3-nitro-5-fluorophenyl)methylamino)piperidine (Preparation 28) (0.06 g, 0.22 mmol), iron dust (0.06 g, 1.12 mmol), methanol (5 mL) and 1M HCl (0.22 mL, 0.22 mmol), stir, and heat at reflux for 18 hr. Cool the reaction mixture to ambient temperature, dilute with ethyl acetate (50 mL), and add 1N sodium hydroxide solution until basic (pH=9). Separate organic layer, wash with saturated aqueous NaCl solution, dry over sodium sulfate, filter, and concentrate to obtain 0.036 g (69%) of the title intermediate: 1H NMR (CDCl3): 5.9 (m, 1H), 5.7 (m, 2H), 3.6 (bs, 2H), 3.4 (m, 1H), 2.9 (m, 2H), 2.7 (s, 3H), 2.3 (s, 3H), 2.0 (m, 2H), 1.8 (m, 2H), 1.7 (m, 2H).

Workup

  1. temperatureheat
  2. temperatureat reflux for 18 hr
  3. washSeparate organic layer, wash with saturated aqueous NaCl solution
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-b8ab658e7b764f0e96d336c3a7ced2d3
Source dataset
uspto-grants-2010_09
Patent number
US07803813B2

Reaction notes

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