Methylamine → HCID 78135728, compound

HRID 626116Notes

Reaction equation

HRID 626116 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:12]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH3:15])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10]Br.[CH3:29][NH2:30]>CO>[Br:1][C:2]1[CH:3]=[C:4]([C:12]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH3:15])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][CH2:10][NH:30][CH3:29]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 121266696HCID 121266696, compound

Product 1

HCID 78135728HCID 78135728, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the same procedure as described in example 11, step D, 4-(1-(3-bromo-4-(2-bromoethoxy)phenyl)-2-phenylbut-1-enyl)phenol (0.09 g, 1.0 eq) was reacted with MeNH2 (30% wt in water, 10 mL) in MeOH (20 mL) under reflux to give 73 mg desired product (90% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.40 (s, 1H), 6.98-7.20 (m, 7H), 6.87 (d, J=8.4 Hz, 1H), 6.78 (d, J=8.4 Hz, 1H), 6.68 (d, J=8.8 Hz, 1H), 6.45 (d, J=8.4 Hz, 1H), 4.17 (t, J=5.2 Hz, 1H), 4.01 (t, J=4.8 Hz, 1H), 3.06 (t, J=4.8 Hz, 1H), 2.96 (t, J=5.2 Hz, 1H), 2.40-2.60 (m, 5H), 0.88 (t, J=5.2 Hz, 3H); m/z=452 [M+1]+.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-1e7a97a1fb5c4c1db5b28a7bcd755ad6
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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