Hydrochloric Acid → N-[3-(4-Nitrophenoxy)propyl]methylamine Hydrochloride

HRID 1091095Notes

Reaction equation

HRID 1091095 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH2:10][CH2:11]I)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:15][NH2:16].[ClH:17]>C(O)C>[ClH:17].[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([O:8][CH2:9][CH2:10][CH2:11][NH:16][CH3:15])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 156758901-(4-Nitrophenoxy)-3-iodopropane

Product 1

HCID 67917252N-[3-(4-Nitrophenoxy)propyl]methylamine Hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Nitrophenoxy)-3-iodopropane (4.76 g, 15.50 mmol) was added portionwise to a stirring solution of methylamine (33%) in ethanol (100 mL) at 0° C. The mixture stirred at room temperature for 4 hours and was then concentrated. The residue was partitioned between ethyl acetate/10% aqueous K2CO3. The organic phase was dried, decolorized and concentrated to afford an oil which was treated with ethanolic HCl. Yield: 2.5 g of hydrochloride salt which was used without purification.

Workup

  1. concentrationwas then concentrated
  2. customThe residue was partitioned between ethyl acetate/10% aqueous K2CO3
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customto afford an oil which
  6. customYield: 2.5 g of hydrochloride salt which was used without purification

Sources & evidence

ORD record
ord-22e8598325524ba8b614bebefda527e1
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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