Diisopropylethylamine → 6-{[1-(2,6-Dimethoxybenzyl)piperidin-4-yl]isopropylcarbamoyl}hexanoic Acid Ethyl Ester
Reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][CH:17]=[C:16]([O:20][CH3:21])[C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([NH:12][CH:13]([CH3:15])[CH3:14])[CH2:8][CH2:7]1.C(N(CC)C(C)C)(C)C.[CH2:31]([O:33][C:34](=[O:43])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40](Cl)=[O:41])[CH3:32]>ClCCl>[CH2:31]([O:33][C:34](=[O:43])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][C:40](=[O:41])[N:12]([CH:9]1[CH2:10][CH2:11][N:6]([CH2:5][C:4]2[C:3]([O:2][CH3:1])=[CH:19][CH:18]=[CH:17][C:16]=2[O:20][CH3:21])[CH2:7][CH2:8]1)[CH:13]([CH3:15])[CH3:14])[CH3:32]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of [1-(2,6-dimethoxybenzyl)piperidin-4-yl]isopropylamine (1.3 g, 4.6 mmol) and N,N-diisopropylethylamine (1.2 mL, 9.9 mmol) in dichloromethane (40 mL) was cooled to 0° C. under nitrogen. 6-Chlorocarbonylhexanoic acid ethyl ester (0.73 mL, 5.0 mmol) was added dropwise and the reaction mixture was stirred at 0° C. for 2 h and then at room temperature for an additional 2 h. The reaction mixture was then transferred to a separatory funnel and washed with NaHCO3 (2×) and brine (1×). The organic layer was then dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to afford the title intermediate as a yellow oil (2.2 g), which was used without further purification.
Workup
- waitat room temperature for an additional 2 h
- customThe reaction mixture was then transferred to a separatory funnel
- washwashed with NaHCO3 (2×) and brine (1×)
- dry with materialThe organic layer was then dried over anhydrous magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-d7f124cfd3904852b63014b3b4f98d00
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08080565B2
Reaction notes
Loading…