Diisopropylethylamine → tert-Butyl 1-(2-chloropyridin-4-yl)piperidin-4-ylcarbamate
Reaction equation
[Cl:1][C:2]1C=C(F)C=[CH:4][N:3]=1.[C:9]([N:16]1CCC(N)C[CH2:17]1)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH3:23][CH2:24][N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])C>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:30]=[C:29]([N:25]2[CH2:24][CH2:23][CH:17]([NH:16][C:9](=[O:10])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:28][CH2:26]2)[CH:31]=[CH:4][N:3]=1Participants
5
Procedure
To a mixture of 2-chloro-4-fluoropyridine (1.00 g, 7.60 mmol) and Boc-4-aminopiperidine (1.98 g, 9.09 mmol) in NMP (10 mL) was added DIPEA (1.86 mL, 10.6 mmol). Argon was bubbled through the cloudy solution for 5 minutes before the reaction mixture was heated in the microwave for 2×30 minutes to 150° C. The mixture was then poured into water and extracted with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and evaporated. Purification by chromatography (silica gel, 50 g, 0 to 50% ethyl acetate in heptane) afforded the title compound (1.47 g, 62%) as a white solid.
Workup
- customArgon was bubbled through the cloudy solution for 5 minutes before the reaction mixture
- temperaturewas heated in the microwave for 2×30 minutes to 150° C
- additionThe mixture was then poured into water
- extractionextracted with ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulfate
- filtrationfiltered
- customevaporated
- customPurification by chromatography (silica gel, 50 g, 0 to 50% ethyl acetate in heptane)
Sources & evidence
- ORD record
- ord-d8c65f2b3465459da5ec5a34c81cb3bb
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08486967B2
Reaction notes
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