Piperidine → 2-Piperidin-1-yl-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acetamide

HRID 643261Notes

Reaction equation

Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]([N:14]2[CH2:20][C:19]3([CH3:22])[CH2:21][CH:15]2[CH2:16][C:17]([CH3:24])([CH3:23])[CH2:18]3)=[O:13])=[CH:8][CH:7]=1)=[O:4].[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.CCN(C(C)C)C(C)C>CC(C)=O.CC#N>[N:25]1([CH2:2][C:3]([NH:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]([N:14]3[CH2:20][C:19]4([CH3:22])[CH2:21][CH:15]3[CH2:16][C:17]([CH3:24])([CH3:23])[CH2:18]4)=[O:13])=[CH:8][CH:7]=2)=[O:4])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 2-chloro-N-[4-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]octane-6-carbonyl)-phenyl]-acetamide (40 mg, 0.115 mmol) in acetone (250 μl) was added to a mixture of piperidine (17.1 μl, 0.173 mmol) and DIPEA (40 μl, 0.229 mmol) in MeCN (250 μl). The resulting reaction mixture was heated and stirred in a microwave oven for 10 min. at 100° C. After cooling to room temperature the volatiles were removed in vacuo and the residue purified on a prep. Gilson HPLC. Pure fractions were collected, evaporated in vauco and dried at 50° C. for 16 hours affording 43.8 mg (75%) of the title compounds as a TFA salt.

Workup

customThe resulting reaction mixture
temperaturewas heated
temperatureAfter cooling to room temperature the volatiles
customwere removed in vacuo
customthe residue purified on a prep
customPure fractions were collected
customevaporated in vauco
customdried at 50° C. for 16 hours

Sources & evidence

ORD record: ord-b521292d31e14319a593a534ebda5712
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700583B2

Reaction notes

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