Methylamine → 3-Diphenylmethoxy-1-methylazetidine

HRID 654081Notes

Reaction equation

HRID 654081 reaction equation
Cl[CH2:2][CH:3]([O:6][CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:4]Cl.[CH3:20][NH2:21]>>[C:8]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[O:6][CH:3]2[CH2:4][N:21]([CH3:20])[CH2:2]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 123293381,3-Dichloro-2-diphenylmethoxypropane

Product 1

HCID 198883633-Diphenylmethoxy-1-methylazetidine

Procedure

A solution of 244. g (0.83 mole) of 1,3-dichloro-2-diphenylmethoxypropane in 300 ml of methylamine was heated in a steel bomb to 100° for 18 hours. The mixture was concentrated, and the residue partitioned between chloroform and dilute hydrochloric acid. The acid solution was washed twice with chloroform, and the chloroform solutions combined. The chloroform was extracted with dilute sodium hydroxide, dried with sodium sulfate, and concentrated. The residue was distilled (b.p. 125°-130°/0.1 mm) to yield 104 g (40%). The distillate crystallizes on standing and can be recrystallized from isooctane, mp 44°-48°.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue partitioned between chloroform and dilute hydrochloric acid
  3. washThe acid solution was washed twice with chloroform
  4. extractionThe chloroform was extracted with dilute sodium hydroxide
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated
  7. distillationThe residue was distilled (b.p. 125°-130°/0.1 mm)
  8. customto yield 104 g (40%)
  9. customThe distillate crystallizes on standing
  10. customcan be recrystallized from isooctane, mp 44°-48°

Sources & evidence

ORD record
ord-bd305e8849c54c68bf5833864a402d91
Source dataset
uspto-grants-1992_07
Patent number
US05130309

Reaction notes

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