Triethylamine → Acetic acid 1-benzyl-4-[methyl-(4-trifluoromethoxy-phenyl)-carbamoyl]-piperidin-4-yl ester
Reaction equation
[C:1]([O:4][C:5]1([C:18]([OH:20])=O)[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:7][CH2:6]1)(=[O:3])[CH3:2].CCN(CC)CC.CCN(C(C)C)C(C)C.[CH3:37][NH:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][C:46]([F:49])([F:48])[F:47])=[CH:41][CH:40]=1.OS([O-])(=O)=O.[K+]>C(Cl)Cl.CN(C=O)C>[CH2:11]([N:8]1[CH2:7][CH2:6][C:5]([O:4][C:1](=[O:3])[CH3:2])([C:18](=[O:20])[N:38]([CH3:37])[C:39]2[CH:44]=[CH:43][C:42]([O:45][C:46]([F:47])([F:48])[F:49])=[CH:41][CH:40]=2)[CH2:10][CH2:9]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 1.4 g (5 mmol) 4-acetoxy-1-benzyl-piperidine-4-carboxylic acid 0.49 mL (5.8 mmol) oxalylchloride, cat. amount DMF and 2.1 mL (15 mmol) NEt3 in DCM at 0° C. was stirred for 1 h. The mixture was concentrated and to 0.79 g (2.42 mmol) of the acid chloride and 2.1 mL (12.1 mmol) DIPEA in 25 mL DCM was added 0.554 g (2.9 mmol) methyl-(4-trifluoromethoxy-phenyl)-amine. The mixture was stirred for 15 h at room temperature. KHSO4 (1N) was added and the mixture was extracted with DCM. The combined organic extracts were dried with MgSO4 and evaporated. 0.782 g (72%) of the title compounds as obtained. MS (m/e): 451.3 [(M+H)+].
Workup
- customat 0° C.
- stirringThe mixture was stirred for 15 h at room temperature
- extractionthe mixture was extracted with DCM
- dry with materialThe combined organic extracts were dried with MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-feddd21363f24556bcb0256c0d248376
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399676B2
Reaction notes
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