Piperidine → 4-(Piperidine-1-carbonyl)benzaldehyde
Reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=O.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[NH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1>C(Cl)Cl.CCOCC>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:3])=[CH:5][CH:6]=1)=[O:9]Participants
7
Procedure
Synthesis of these compounds was begun by suspending 4-carboxybenzaldehyde (34.5 mmol) in 50 mL CH2Cl2, adding 5 mL triethylamine and, after 5 minutes, 4.25 mL pivaloyl chloride. After 1.5 hours, 3.42 mL piperidine was added to the stirred reaction and, after 2 hours, the solution was diluted with ether and washed two times with 5% NaHCO3, three times with dilute HCl, and finally a saturated solution of NaCl. The organic solution was dried over Na2SO4 and the solvents were removed on a rotary evaporator to yield 7.38 g of 1-(4'-formylbenzoyl)piperidine.
Workup
- customSynthesis of these compounds
- waitAfter 1.5 hours
- washwashed two times with 5% NaHCO3, three times with dilute HCl
- dry with materialThe organic solution was dried over Na2SO4
- customthe solvents were removed on a rotary evaporator
Sources & evidence
- ORD record
- ord-0016a03370444060b77b2973e443b61c
- Source dataset
- uspto-grants-1998_07
- Patent number
- US05783587
Reaction notes
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