4-(Aminomethyl)-1-(1-phenylethyl)piperidin-4-amine → HCID 178435989, compound

HRID 2281588Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-2-methyl-isothiourea (Intermediate A) (1.7 g, 4.54 mmol) and 4-aminomethyl-1-(1-phenyl-ethyl)-piperidin-4-ylamine (Intermediate BM) (1.6 g, 4.59 mmol) in propan-2-ol (50 ml) is stirred at 80° C. for 16 hours. The reaction mixture is concentrated in vacuo and purified by column chromatography (basic alumina, 0-2% MeOH in DCM) to obtain pale yellow solid. The compound obtained is further dissolved in MeOH and precipitated by adding diethyl ether. The supernatant solvent mixture is decanted and the product is washed again with diethyl ether and dried under vacuum to afford the title compound as off-white solid; [M+H]+ 429

Workup

concentrationThe reaction mixture is concentrated in vacuo
custompurified by column chromatography (basic alumina, 0-2% MeOH in DCM)
customto obtain pale yellow solid
customThe compound obtained
customprecipitated
additionby adding diethyl ether
customThe supernatant solvent mixture is decanted
washthe product is washed again with diethyl ether
customdried under vacuum

Sources & evidence

ORD record: ord-cf3f906a0bc246808bd74756c5481f67
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139586B2

Reaction notes

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