Triethylamine → HCID 9822274, compound
Reaction equation
[CH:1]1([C:7](Cl)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N:18]1[CH2:23][CH2:22][N:21]([CH2:24][CH:25]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]2)[CH2:20][CH2:19]1.C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([C:7]([N:27]2[CH2:28][CH2:29][CH2:30][CH:25]([CH2:24][N:21]3[CH2:22][CH2:23][N:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[O:11][CH3:10])[CH2:19][CH2:20]3)[CH2:26]2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Cyclohexanecarbonyl chloride (0.506 g, 3.5 mmol) was added to a solution of 1-(2-methoxyphenyl)-4-piperidin-3-ylmethyl-piperazine (1.0 g, 3.5 mmol) from example 6 and triethylamine (2 equivalents, 1 mL) in CH2Cl2 (30 mL) and the solution stirred under N2 at 0° C. for 16 hours. The mixture was concentrated under vacuum, water (50 mL) added and the product extracted into ethyl acetate (3×25 mL). The combined organics were washed with water (25 mL), saturated sodium bicarbonate (20 mL) and brine (25 mL). After drying over sodium sulfate, filtration and concentration under vacuum afforded the titled product (1.13 g, 81% yield). An ethanolic solution of the product was treated with a hot ethanolic solution of fumaric acid (1.0 equivalents) and afforded the fumarate salt of the titled compound as a light yellow colored solid.
Workup
- concentrationThe mixture was concentrated under vacuum, water (50 mL)
- additionadded
- extractionthe product extracted into ethyl acetate (3×25 mL)
- washThe combined organics were washed with water (25 mL), saturated sodium bicarbonate (20 mL) and brine (25 mL)
- dry with materialAfter drying over sodium sulfate, filtration and concentration under vacuum
Sources & evidence
- ORD record
- ord-60fca1c95308480683e1a726bba3c23e
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06255302B1
Reaction notes
Loading…