C-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-methyleneamine → 1-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-ethylamine

HRID 2370509Notes

Reaction equation

HRID 2370509 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]=[NH:12])[C:5]=2[O:4][CH2:3][CH2:2]1.[CH3:13][Mg]Br>C1(C)C=CC=CC=1.C(OCC)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([CH:11]([NH2:12])[CH3:13])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 86618567C-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-methyleneamineHCID 178418573HCID 178418573, compound

Product 1

HCID 577255011-(2,3-Dihydro-benzo[1,4]dioxin-5-yl)-ethylamine

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

The dried resin to which the C-(2,3-dihydro-benzo[1,4]dioxin-5-yl)-methyleneamine (1 eq) was bound was suspended in dry toluene. Under a nitrogen atmosphere methyl magnesium bromide (150 eq) in a 3 M solution in ethyl ether was added. This mixture was shaken for 24 hours at 60° C. then filtered and washed with toluene, water, then methanol and dichloromethane alternately three times. The final wash was with methanol. The solid was dried under vacuum.

Workup

  1. filtrationthen filtered
  2. washwashed with toluene, water
  3. washThe final wash
  4. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-1cbd833b737b494c9a77c1f14815c286
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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