Methyl 4-(chloromethyl)benzoate → Methyl 4-((4-methylpiperazin-1-yl)methyl)benzoate
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=2)[CH2:4][CH2:3]1.Cl[CH2:19]C1C=CC(C(O)=O)=CC=1.COC(=O)C1C=CC(CCl)=CC=1.CN1CCNCC1>>[CH3:19][O:14][C:13](=[O:15])[C:12]1[CH:16]=[CH:17][C:9]([CH2:8][N:5]2[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]2)=[CH:10][CH:11]=1Participants
Procedure
4-(4-methylpiperazin-1-ylmethyl)benzoic acid (17) is obtained as described in the following Scheme 5. 4-Chloromethylbenzoic acid (14) is first esterified to a methyl ester to protect an acid group in the following reaction. 4-Chloromethyl-benzoic acid methyl ester (15) is then allowed to react with 1-methylpiperazine to give 4-(4-methylpiperazin-1-ylmethyl)benzoic acid methyl ester (16). Methyl ester is cleaved by heating with potassium hydroxide in methanol. 4-(4-methylpiperazin-1-ylmethyl)benzoic acid is reacted as described above in Scheme 4 with aminopyridine derivatives (3) to result in N-4-(4-methylpiperazin-1-ylmethyl)benzamide derivatives of (13). By a similar manner other N-4-(piperazin-1-ylmethyl)benzamide derivatives of (13) can be prepared.
Workup
- customin the following reaction
Sources & evidence
- ORD record
- ord-bdb3d586ca31405287b013627fd32c94
- Source dataset
- uspto-grants-2009_01
- Patent number
- US07482340B2
Reaction notes
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