3-{3-[(Pyrrolidin-1-yl)methyl]phenoxy}propan-1-amine → HCID 20232126, compound

HRID 2290380Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4](SC)[N:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N:16]1([CH2:21][C:22]2[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=2)[O:25][CH2:26][CH2:27][CH2:28][NH2:29])[CH2:20][CH2:19][CH2:18][CH2:17]1>C(Cl)(Cl)Cl>[N:16]1([CH2:21][C:22]2[CH:23]=[C:24]([CH:30]=[CH:31][CH:32]=2)[O:25][CH2:26][CH2:27][CH2:28][NH:29][C:4]2[N:5]=[N:6][C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[C:2]([CH3:1])[N:3]=2)[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 5-methyl-3-methylthio-6-phenyl-1,2,4-triazine (2.17 g) and 3-[3(1-pyrrolidinylmethyl)phenoxy]propylamine (3.04 g) was heated at 150° C. for 33 hours and dissolved in a small volume of chloroform after cooling. The solution was purified by column chromatgraphy on silica gel (100 g) with chloroform and then a mixture of chloroform and methanol (20:1) as eluents to give 3-[3-[3-(1-pyrrolidinylmethyl)-phenoxy]propylamino]-5-methyl-6-phenyl-1,2,4-triazine (2.57 g).

Workup

temperatureafter cooling
customThe solution was purified by column chromatgraphy on silica gel (100 g) with chloroform
additiona mixture of chloroform and methanol (20:1) as eluents

Sources & evidence

ORD record: ord-354e3a225f4346398a3a651cbac995f8
Source dataset: uspto-grants-1986_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04616014

Reaction notes

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