Methylamine → 4-(1-(4-(2-(Methylamino)ethoxy)phenyl)-2-(thiophen-3-yl)but-1-enyl)phenol

HRID 626105Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a stirred solution of 4-(1-(4-(2-chloroethoxy)phenyl)-2-(thiophen-3-yl)but-1-enyl)phenol (0.3 g, 1.0 eq) in 10 mL MeOH was added 10 mL MeNH2 (30% in water). The mixture was refluxed at 80° C. overnight, and purified by column chromatography with CH2Cl2:MeOH(NH3)=10:1 to give the desired product (185 mg, 63% yield, Z/E=1/1). 1H NMR (400 MHz, CDCl3) δ 7.00-7.12 (m, 3H), 6.90-6.95 (m, 1H), 6.80-6.89 (m, 2H), 6.72-6.79 (m, 2H), 6.68-6.72 (m, 1H), 6.58 (d, J=8.8 Hz, 1H), 6.53 (d, J=8.8 Hz, 1H), 4.09 (t, J=5.2 Hz, 1H), 3.99 (t, J=5.2 Hz, 1H), 3.00 (t, J=5.2 Hz, 1H), 2.94 (t, J=5.2 Hz, 1H), 2.40-2.54 (m, 5H), 0.98 (t, J=5.2 Hz, 3H); m/z=380[M+1]+.

Workup

custompurified by column chromatography with CH2Cl2

Sources & evidence

ORD record: ord-e156c02b06c644799f0e8854d7763a4a
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309211B2

Reaction notes

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