3-(Dimethylamino)propyl chloride hydrochloride → {5-[4-(3-Dimethylamino-propoxy)-phenyl]-thiazol-2-yl}phenyl-amine

HRID 1713647Notes

Reaction equation

[C:1]1([NH:7][C:8]2[S:9][C:10]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)=[CH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.Cl[CH2:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26].CC(C)([O-])C.[Na+]>C(O)CCC>[CH3:26][N:25]([CH3:27])[CH2:24][CH2:23][CH2:22][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:10]2[S:9][C:8]([NH:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:12][CH:11]=2)=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 4-(2-phenylamino-thiazol-5-yl)-phenol (35 mg, 0.130 mmol), 1-chloro-3-dimethylaminopropane hydrochloride (27 mg, 0.170 mmol, 1.3 equiv), and sodium tert-butoxide (29.6 mg, 0.299 mmol, 2.3 equiv) in 1-butanol (0.2 mL) is heated to 100° C. (using a preheated oil bath) for 3.5 h. The reaction mixture is allowed to cool to RT and concentrated in vacuo. Purification of the crude material by silica gel (10 g) column chromatography (CH2Cl2/MeOH, 90/10→80/20) affords the title compound as a reddish solid: ES-MS: 354.0 [M+H]+; single peak at tR=6.27 min (System 1); Rf=0.09 (CH2Cl2/MeOH, 90/10).

Workup

temperatureto cool to RT
concentrationconcentrated in vacuo
customPurification of the crude material by silica gel (10 g) column chromatography (CH2Cl2/MeOH, 90/10→80/20)

Sources & evidence

ORD record: ord-4f0ba443b1ea4751a27bc7830cb89a2e
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795288B2

Reaction notes

Loading…