Formamide → 3-(1-Propyl-4-piperidinyl)benzamide
Reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]2[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH3:18])[CH2:12][CH2:11]2)[CH:5]=1.C([NH2:22])=O.C[O-].[Na+]>CN(C=O)C.CO>[CH2:16]([N:13]1[CH2:14][CH2:15][CH:10]([C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([NH2:22])=[O:2])[CH2:11][CH2:12]1)[CH2:17][CH3:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 3-(1-Propyl-piperidin-4-yl)-benzoic acid methyl ester (0.6 g) and formamide (320 μL) in DMF (9 ml) was heated to 100° C. under a blanket of argon. Sodium methoxide in methanol (30%, 770 μL) was added dropwise and after 1 h, GC analysis revealed the complete absence of starting material and indicated the titled compound as the sole product. After cooling, CH2Cl2 was added and the resulting solution was filtered through a pad of celite and evaporated to dryness. The residue was chromathographed on a silica column using MeOH: CH2Cl2 (1:3 (v/v)) as eluent. The fractions containing pure titled compound were collected, and the solvent was removed in vacuum, affording 400 mg of the titled compound. m.p. 182° C. (oxalate) (MS m/z (rel. intensity, 70 eV) 246 (M+, 4), 217 (bp), 131 (19), 100 (22), 70 (63).
Sources & evidence
- ORD record
- ord-2106e71dbc7d40da8f40d8363b4b6991
- Source dataset
- uspto-grants-2016_08
- Patent number
- USRE046117E1
Reaction notes
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