4-Methylmorpholine → 4-[[4-(1-Methylpropyl)-1-piperazinyl]carbonyl]benzaldehyde
Reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1)=[O:2].Cl.CN(C)CCCN=C=NCC.O.O[N:26]1[C:30]2[CH:31]=CC=[CH:34][C:29]=2N=N1.C[N:36]1[CH2:41][CH2:40]O[CH2:38][CH2:37]1>C(Cl)Cl>[CH:30]([N:26]1[CH2:40][CH2:41][N:36]([C:7]([C:6]2[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:11][CH:10]=2)=[O:9])[CH2:37][CH2:38]1)([CH2:29][CH3:34])[CH3:31]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The product of Example 6 (3.2 g) and 4-formylbenzoic acid (2.102 g) were suspended in DCM (130 mL) under nitrogen. 1-{3-(Dimethylamino)propyl}-3-ethylcarbodiimide hydrochloride (3.96 g), 1-hydroxybenzotriazole hydrate (3.06 g) and N-methylmorpholine (9.432 g) were added in sequence to the above suspension. The reaction mixture was stirred under nitrogen for 24 h. DCM (100 mL) was added, the resulting mixture was washed with 10% aqueous NaOH solution (2×50 mL) and water (2×100 mL), and the separated organic phase was dried over anhydrous MgSO4, and concentrated under reduced pressure to yield the crude product (3.75 g). Chromatography of the residue on silica gel (2-5% 2 M methanolic ammonia/DCM) yielded the title compound (2.75 g).
Workup
- washthe resulting mixture was washed with 10% aqueous NaOH solution (2×50 mL) and water (2×100 mL)
- dry with materialthe separated organic phase was dried over anhydrous MgSO4
- concentrationconcentrated under reduced pressure
- customto yield the crude product (3.75 g)
Sources & evidence
- ORD record
- ord-e678d8141d8d4ff9af3f39c4597fbeba
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07414047B2
Reaction notes
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