Diisopropylethylamine → N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-3-hydroxy-5-methoxy-benzamide
Reaction equation
Cl.[OH:2][C:3]1[CH:4]=[C:5]([CH:15]=[C:16]([O:18][CH3:19])[CH:17]=1)[C:6]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)=[O:7].C(OC(N1CCC(NC(=O)C2C=C(OC)C=C(O)C=2)CC1)=O)(C)(C)C.Cl.O1CCOCC1.[CH2:52]([O:54][C:55]1[CH:56]=[C:57]([CH:60]=[C:61]([O:64][CH2:65][CH3:66])[C:62]=1[F:63])[CH:58]=O)[CH3:53].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>CCO.C(O)(=O)C>[CH2:52]([O:54][C:55]1[CH:56]=[C:57]([CH:60]=[C:61]([O:64][CH2:65][CH3:66])[C:62]=1[F:63])[CH2:58][N:12]1[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[C:5]2[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=[C:3]([OH:2])[CH:4]=2)[CH2:14][CH2:13]1)[CH3:53]Participants
9
Reactant 6
HCID 81531Diisopropylethylamine
HCID 5003444Sodium cyanoborohydride
HCID 204431481,4-Dioxane hydrochloride
HCID 591282733,5-Diethoxy-4-fluoro-benzaldehyde
HCID 684558663-hydroxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride
HCID 684587374-(3-Hydroxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl esterProduct 1
Reagents, catalysts & solvents 2
Procedure
In analogy to the procedure described in example 50k), 3-hydroxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride [prepared from 4-(3-hydroxy-5-methoxy-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester (example 168a) by Boc cleavage using HCl/dioxane in EtOH at rt in analogy to the procedure described in example 250b)] was reacted with 3,5-diethoxy-4-fluoro-benzaldehyde (example 50 g), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as colorless solid. MS: 447.2 (MH+).
Workup
- customat rt
Sources & evidence
- ORD record
- ord-f5fca5315ab14fe2a8ed216f08cf00b6
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772253B2
Reaction notes
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