Methylamine → HCID 15053461, compound

HRID 2081489Notes

Reaction equation

HRID 2081489 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11](Cl)=[O:12])[CH2:8]1.[CH3:17][NH2:18]>O1CCCC1.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[O:6][CH:7]1[CH2:10][N:9]([C:11]([NH:18][CH3:17])=[O:12])[CH2:8]1

Participants

5

Reactant 2

HCID 6329MethylamineHCID 19799594HCID 19799594, compound

Product 1

HCID 15053461HCID 15053461, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4.8 g (0.02 mole) of 3-(3-methoxyphenoxy)-1-azetidinecarbonyl chloride in 20 ml of tetrahydrofuran was treated with 4.7 g (0.06 mole) of 40% aqueous monomethylamine and stirred for 16 hr. The reaction mixture was diluted with 200 ml of water and the oil which separated was extracted into methylene chloride (2×50 ml). The extracts were dried by passing through Whatman phase separating paper and concentrated in vacuo (3.85 g). The residue was purified by chromatography on two 4 mm (silica gel) chromatotron plates by eluting with an ethyl acetate/methylene chloride gradient to give 0.98 g (21%) of tan solid. Recrystallization from benzene with a trace of ligroin yielded 600 mg of tan crystalline powder, m.p. 109°-111° C.

Workup

  1. customthe oil which separated
  2. extractionwas extracted into methylene chloride (2×50 ml)
  3. customThe extracts were dried
  4. customseparating paper
  5. concentrationconcentrated in vacuo (3.85 g)
  6. customThe residue was purified by chromatography on two 4 mm (silica gel) chromatotron plates
  7. washby eluting with an ethyl acetate/methylene chloride gradient

Sources & evidence

ORD record
ord-85fe641c60a7445b9a1f640abfb1a706
Source dataset
uspto-grants-1993_02
Patent number
US05183902

Reaction notes

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