Dicyclohexylcarbodiimide → Tert-butyl 4-(3-(4-fluorophenoxy)phenylcarbamoyl)-4-methylpiperidine-1-carboxylate

HRID 216019Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:17])([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:18][C:19]1[CH:32]=[CH:31][C:22]([O:23][C:24]2[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=2)[NH2:27])=[CH:21][CH:20]=1.C1CCC(N=C=NC2CCCCC2)CC1.C1C=NC2N(O)N=NC=2C=1>CCOC(C)=O.CN(C=O)C>[F:18][C:19]1[CH:32]=[CH:31][C:22]([O:23][C:24]2[CH:25]=[C:26]([NH:27][C:14]([C:11]3([CH3:17])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]3)=[O:16])[CH:28]=[CH:29][CH:30]=2)=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1-(tert-butoxycarbonyl)-4-methylpiperidine-4-carboxylic acid (243 mg, 1.0 mmol), 3-(4-fluorophenoxy)aniline (203 mg, 1.0 mmol), DCC (206 mg, 1.0 mmol), and HOAt (138 mg, 1.01 mmol) were combined in EtOAc (50 mL) and DMF (5 mL). The reaction mixture was heated at 80° C. for 20 hours. Most of the EtOAc was evaporated, resulting in precipitation of a solid, which was removed by filtration. The filtrate was diluted with EtOAc, washed with 1 N aq. HCl, water, and brine, dried, and concentrated under vacuum to give the title compound. MS (ES+) [M+H]+=429.

Workup

customMost of the EtOAc was evaporated
customresulting in precipitation of a solid, which
customwas removed by filtration
additionThe filtrate was diluted with EtOAc
washwashed with 1 N aq. HCl, water, and brine
customdried
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-6984cfa846b849f798264fda96d7ebfc
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08193202B2

Reaction notes

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