4-Piperidinepropanamine,1-methyl-(9CI) → HCID 68439408, compound

HRID 1786153Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9](S(CC)(=O)=O)=[N:10][CH:11]=1)=[O:5])[CH3:2].[CH3:18][N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH2:27][NH2:28])[CH2:21][CH2:20]1>CCO>[CH2:1]([O:3][C:4]([C:6]1[C:7]([CH3:17])=[N:8][C:9]([NH:28][CH2:27][CH2:26][CH2:25][CH:22]2[CH2:21][CH2:20][N:19]([CH3:18])[CH2:24][CH2:23]2)=[N:10][CH:11]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-ethanesulfonyl-4-methyl-pyrimidine-5-carboxylic acid ethyl ester (0.30 g, 1.18 mmol) and 3-(1-methyl-piperidin-4-yl)-propylamine (0.18 mg, 1.10 mmol) in EtOH (3 mL) was heated in a sealed tube at 100° C. for 6 h. The mixture was concentrated and purified by FCC to give 200 mg (53%). 1H NMR (CDCl3): 8.88-8.72 (m, 1H), 5.60-5.44 (m, 1H), 4.31 (q, J=7.2 Hz, 2H), 3.52-3.39 (m, 2H), 2.91-2.77 (m, 2H), 2.64 (s, 3H), 2.26 (s, 3H), 1.94-1.85 (m, 2H), 1.72-1.57 (m, 4H), 1.41-1.20 (m, 8H).

Workup

concentrationThe mixture was concentrated
custompurified by FCC
customto give 200 mg (53%)

Sources & evidence

ORD record: ord-d021555713be4ce78de4cd74f87a0d5a
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07507737B2

Reaction notes

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