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

HRID 1988419Notes

Reaction equation

HRID 1988419 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-52c249de9ebb4430914271b157d44391
Source dataset
uspto-grants-2009_06
Patent number
US07553854B2

Reaction notes

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