N-Methylbenzylamine → Benzenemethanamine, N-pentyl-
Reaction equation
[CH3:1][CH:2](NCCC(O)=O)[CH2:3][CH2:4]CC.[CH3:13][NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.BrCCCCC.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Na+].[Na+].C(=O)(O)[O-].[Na+].C(=O)(O)[O-].[K+]>>[CH2:13]([NH:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:1][CH2:2][CH2:3][CH3:4]Participants
Procedure
The present invention also provides a process for the synthesis of 3-[N-(methylpentyl)amino]propionic acid (III) wherein N-methylbenzylamine is reacted with 1-bromo pentane in presence of a base like potassium carbonate, sodium carbonate, sodium bicarbonate, potassium bicarbonate preferably potassium carbonate to get N-methyl, N-pentyl benzyl amine (VI) which is subjected to debenzylation using 10% Pd/C as catalyst in an alcoholic solvent to get N-methyl, N-pentylamine (V) which is isolated in pure form as an acid addition salt of an organic acid such as fumaric acid, citric acid, maleic acid, edetic acid preferably it is isolated as an oxalate salt. Compound (V) is reacted with methyl-3-halopropionate like methyl 3-chloro propionate, methyl-3-bromo propionate, methyl 3-iodo propionate more preferably methyl-3-bromo propionate in a suitable solvent preferably toluene in the presence of a base preferably potassium carbonate at a temperature ranging from 25° C. to 80° C. preferably at 70° C. to get 3-[N-(methylpentyl)amino]propionate (IV), which is further hydrolyzed to give 3-[N-(methylpentyl)amino]propionic acid hydrochloride (III) which is the key intermediate for the synthesis of Ibandronate sodium.
Workup
- customThe present invention also provides a process
Sources & evidence
- ORD record
- ord-b526f897437b421f9b39d539f1c5b8ad
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178712B2
Reaction notes
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