N-(2-Aminoethyl)piperidine → HCID 178420276, compound

HRID 892114Notes

Reaction equation

[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:14][C:15]=3[N:16]=[C:17]2Cl)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:26]1([CH2:32][CH2:33][NH2:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:1]([C@@H:8]1[CH2:19][N:18]2[C:10]([C:11]3[NH:12][C:13]([CH:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[N:14][C:15]=3[N:16]=[C:17]2[NH:34][CH2:33][CH2:32][N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Compound 67a (100 mg, 0.240 mmol) obtained in Example 67 was dissolved in tetrahydrofuran (2 mL), and to the solution were added 2-piperidinoethylamine (61 μL, 0.480 mmol, 2.0 equivalents) and N,N-diisopropylethylamine (344 μL, 0.960 mmol, 4.0 equivalents) and the mixture was stirred at 80° C. for 2 hours. The reaction mixture was concentrated, and then the residue was purified by silica gel column chromatography (chloroform:methanol=90:10, chloroform: a 7 mol/L ammonia/methanol solution=90:10). To the product was added diisopropyl ether, and the deposited crystals were collected by filtration and dried to obtain the title compound (110 mg, 94%) as white crystals.

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel column chromatography (chloroform
additionTo the product was added diisopropyl ether
filtrationthe deposited crystals were collected by filtration
customdried

Sources & evidence

ORD record: ord-52e8bb42735b40949ad6696eb1e737e8
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005430B2

Reaction notes

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