Ethyl 4-amino-1-piperidinecarboxylate → HCID 68695765, compound

HRID 1990873Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-methylsulfanyl-benzooxazole-5-sulfonic acid dimethylamide (1.43 g, 5.25 mmol, 1.0 equiv) and ethyl 4-amino-1-piperidine carboxylate (1.36 g, 7.88 mmol, 1.5 equiv) in anhydrous DMAc (7.5 mL) was heated to 100° C. for 48 h. The solution was concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with ethyl acetate/hexane (2:1) to give 1.40 g (67%) of the title compound. 1H NMR (300 MHz, DMSO): δ 1.19 (t, J=7.1 Hz, 3H), 1.37-1.49 (m, 2H), 1.94-1.99 (m, 2H), 2.59 (s, 6H), 2.94-3.02 (m, 2H), 3.80-3.83 (m, 1H), 3.91-3.95 (m, 2H), 4.04 (q, J=7.1 Hz, 2H), 7.39 (dd, J=8.2 Hz, J=1.8 Hz, 1H), 7.53 (d, J=1.8 Hz, 1H), 7.59 (d, J=8.2 Hz, 1H), 8.39 (d, J=7.6 Hz, 1H). 13C NMR (75 MHz, DMSO): δ 14.56, 31.07, 37.62, 42.05, 49.70, 60.65, 108.88, 114.22, 120.40, 130.37, 143.98, 150.67, 154.59, 162.76. MS (ISP): 397.0 [M+H]+.

Workup

concentrationThe solution was concentrated by evaporation under reduced pressure
customthe crude reaction product
custompurified with column chromatography on silica eluting with ethyl acetate/hexane (2:1)

Sources & evidence

ORD record: ord-ef96fb7b2d744b1ebd10dbeb608b37c1
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07645753B2

Reaction notes

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