Triethylamine → Ethyl 1-(4-morpholin-4-ylbutyryl)4-piperidinecarboxylate

HRID 413717Notes

Reaction equation

CN(C)CCCN=C=NCC.[O:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=O)[CH2:14][CH2:13]1.[NH:24]1[CH2:34][CH2:33][CH:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:26][CH2:25]1.C(N(CC)CC)C>ClCCl.O.OC1C2N=NNC=2C=CC=1>[N:15]1([CH2:18][CH2:19][CH2:20][C:21]([N:24]2[CH2:34][CH2:33][CH:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:26][CH2:25]2)=[O:23])[CH2:14][CH2:13][O:12][CH2:17][CH2:16]1

Participants

Conditions

Temperature: 20 °C

Procedure

0.95 g of N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide in solution in 20 cm3 of dichloromethane is added, at 20° C., to 1.0 g of 4-morpholinobutyric acid, 0.78 g of ethyl isonipecotate, 2.1 cm3 of triethylamine and 20 mg of hydroxybenzotriazole hydrate, in solution in 80 cm3 of dichloromethane. After stirring for 20 hours at 20° C., the reaction mixture is washed with 20 cm3 of water. The organic phase is dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give a pale yellow oil which is purified by chromatography on a CBT1 alumina column [eluent: dichloromethane/methanol (97/3 by volume)]. 1.30 g of ethyl 1-(4-morpholin-4-ylbutyryl)-4-piperidinecarboxylate are thus obtained in the form of a pale yellow oil.

Workup

washthe reaction mixture is washed with 20 cm3 of water
dry with materialThe organic phase is dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
customto give a pale yellow oil which
customis purified by chromatography on a CBT1 alumina column [eluent: dichloromethane/methanol (97/3 by volume)]

Sources & evidence

ORD record: ord-fa613cddc6664ebd80bb12ffb252d632
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06569854B1

Reaction notes

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