Water → HCID 70873332, compound

HRID 1777355Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10]([C:12]1([CH2:25][CH2:26][CH2:27]Br)[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11])[CH3:8].O>O1CCCC1>[CH2:7]([O:9][C:10]([C:12]1([CH2:25][CH2:26][CH2:27][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:13]1)=[O:11])[CH3:8]

Participants

Conditions

Temperature: 62.5 °C

Procedure

Piperidine (0.13 mL, 0.00132 mol) is added to a solution of 4-(3-bromopropyl)piperidine-1,4-dicarboxylic acid-1-tert-butyl ester-4-ethyl ester (0.1 gm, 0.00026 mol) in tetrahydrofuran (5 mL). The reaction mixture is heated at 60-65° C. for 3 hours. It is then cooled to room temperature, treated with demineralized water (12 mL) and extracted with ethyl acetate (2×20 mL). Combined extract is dried over sodium sulphate and concentrated under reduced pressure to get a crude residue which is purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane, 1:9) to yield 4-(3-piperidin-1-yl propyl)piperidine-1,4-dicarboxylic acid-1-tert-butyl ester-4-ethyl ester.

Workup

temperatureIt is then cooled to room temperature
extractionextracted with ethyl acetate (2×20 mL)
extractionCombined extract
dry with materialis dried over sodium sulphate
concentrationconcentrated under reduced pressure
customto get a crude residue which
customis purified by column chromatography (silica gel 230-400 mesh, methanol:dichloromethane, 1:9)

Sources & evidence

ORD record: ord-a9270880f4354a36980ba98f5de72aec
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266867B2

Reaction notes

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