Methylamine → 4-(2-(4-Hydroxycyclohexyl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-enyl)phenol

HRID 626111Notes

Reaction equation

HRID 626111 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)=[C:12]([CH:15]2[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]2)[CH2:13][CH3:14])=[CH:7][CH:6]=1.[CH3:29][NH2:30]>CO>[OH:21][CH:18]1[CH2:19][CH2:20][CH:15]([C:12]([CH2:13][CH3:14])=[C:11]([C:22]2[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=2)[C:8]2[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][NH:30][CH3:29])=[CH:6][CH:7]=2)[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 1232527154-(1-(4-(2-Chloroethoxy)phenyl)-2-(4-hydroxycyclohexyl)but-1-enyl)phenol

Product 1

HCID 781356114-(2-(4-Hydroxycyclohexyl)-1-(4-(2-(methylamino)ethoxy)-phenyl)but-1-enyl)phenolYield 3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the same procedure as described in example 11, step D, 4-(1-(4-(2-chloroethoxy)phenyl)-2-(4-hydroxycyclohexyl)but-1-enyl)phenol (0.8 g, 1.0 eq) was reacted with MeNH2 (30% wt in water, 10 mL) in MeOH (20 mL) at reflux to give 20 mg desired product (3% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.03 (d, J=8.4 Hz, 2H), 6.94 (d, J=8.4 Hz, 2H), 6.78 (d, J=8.4 Hz, 2H), 6.71 (d, J=8.4 Hz, 2H), 4.04 (t, J=4.8 Hz, 2H), 2.96 (t, J=4.8 Hz, 2H), 2.50 (s, 3H), 2.36-2.47 (m, 1H), 2.04 (q, J=7.6 Hz, 2H), 1.90-2.01 (m, 2H), 1.40-1.80 (m, 6H), 0.87 (t, J=7.6 Hz, 3H); m/z=396[M+1]+.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-484eed3ae3b14267bf453c2548c1d97b
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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