Diisopropylethylamine → N-[1-(3,5-Diisopropoxy-benzyl)-piperidin-4-yl]-5-methoxy-isophthalamic acid methyl ester

HRID 502428Notes

Reaction equation

HRID 502428 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:6]([C:7]([NH:9][CH:10]2[CH2:15][CH2:14][N:13](CC3C=C(OCC)C(F)=C(OCC)C=3)[CH2:12][CH2:11]2)=[O:8])[CH:5]=1.[CH:36]([O:39][C:40]1[CH:41]=[C:42]([CH:45]=[C:46]([O:48][CH:49]([CH3:51])[CH3:50])[CH:47]=1)[CH:43]=O)([CH3:38])[CH3:37].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:6]([C:7]([NH:9][CH:10]2[CH2:11][CH2:12][N:13]([CH2:43][C:42]3[CH:41]=[C:40]([O:39][CH:36]([CH3:38])[CH3:37])[CH:47]=[C:46]([O:48][CH:49]([CH3:51])[CH3:50])[CH:45]=3)[CH2:14][CH2:15]2)=[O:8])[CH:5]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 113106053,5-diisopropoxybenzaldehydeHCID 68458070N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-5-methoxy-isophthalamic acid methyl ester

Product 1

HCID 68456062N-[1-(3,5-Diisopropoxy-benzyl)-piperidin-4-yl]-5-methoxy-isophthalamic acid methyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 5-methoxy-N-piperidin-4-yl-isophthalamic acid methyl ester (example 143) was reacted with 3,5-diisopropoxy-benzaldehyde (example 126b), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50-C to yield the title compound as colorless oil. MS: 499.3 (MH+).

Sources & evidence

ORD record
ord-372fd5b2e2084da480e8eb559dac0645
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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