Piperidine → HCID 9965088, compound
Reaction equation
CC(C[NH:5][C:6](/[CH:8]=[CH:9]/[CH:10]=[CH:11]/C1C=CC2OCOC=2C=1)=O)C.[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([CH2:30][CH2:31][C:32]([OH:34])=O)=[CH:29][C:24]=2[O:23][CH2:22]1.N1CCCCC1.C(N(CC)CC)C.CS(Cl)(=O)=O>ClCCl>[O:21]1[C:25]2[CH:26]=[CH:27][C:28]([CH2:30][CH2:31][C:32]([N:5]3[CH2:6][CH2:8][CH2:9][CH2:10][CH2:11]3)=[O:34])=[CH:29][C:24]=2[O:23][CH2:22]1Participants
Conditions
- Temperature
- 0 °C
Procedure
The method was adapted from that reported for piperlonguminine (section 2.2) but utilising 3-benzo-1,3-dioxol-5-ylpropionic acid and piperidine as the acid and amine components respectively. A mixture of 3-benzo-1,3-dioxol-5-ylpropionic acid (200 mg, 0.0026 mole, 1 eq) and triethylamine (0.27 ml, 0.002 mole, 2 eq) in dichloromethane (50 ml) was stirred for 15 min at 0° C. To this mixture methanesulfonyl chloride (0.11 ml, 0.0015 mole, 1.5 eq) was added and stirred for further 30 min at 0° C. Piperidine (0.15 ml, 0.0015 mole, 1.5 eq) was added to the mixture and stirred for 1 h at 0° C. and 1 h at room temperature. Dichloromethane (50 ml) was added to the mixture which was then washed with 5% HCl (3×100 ml), saturated aqueous NaHCO3 (3×100 ml) and water (3×100 ml). The organic fraction was dried over anhydrous sodium sulphate, filtered and rotary evaporated to yield brown oil (65% yield).
Workup
- stirringstirred for further 30 min at 0° C
- stirringstirred for 1 h at 0° C. and 1 h at room temperature
- washwas then washed with 5% HCl (3×100 ml), saturated aqueous NaHCO3 (3×100 ml) and water (3×100 ml)
- dry with materialThe organic fraction was dried over anhydrous sodium sulphate
- filtrationfiltered
- customrotary evaporated
Sources & evidence
- ORD record
- ord-36b226398c7e4ba7a67d3c14d77011ed
- Source dataset
- uspto-grants-2004_01
- Patent number
- US06680391B2
Reaction notes
Loading…