Diisopropylethylamine → N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-2,6-dimethyl-terephthalamic acid

HRID 502420Notes

Reaction equation

HRID 502420 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]([NH:13][CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)=[O:12])[CH:8]=[C:7]([CH3:20])[C:3]=1[C:4]([OH:6])=[O:5].[CH2:21]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O:33][CH2:34][CH3:35])[C:31]=1[F:32])[CH:27]=O)[CH3:22].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[CH2:21]([O:23][C:24]1[CH:25]=[C:26]([CH:29]=[C:30]([O:33][CH2:34][CH3:35])[C:31]=1[F:32])[CH2:27][N:17]1[CH2:16][CH2:15][CH:14]([NH:13][C:11](=[O:12])[C:9]2[CH:10]=[C:2]([CH3:1])[C:3]([C:4]([OH:6])=[O:5])=[C:7]([CH3:20])[CH:8]=2)[CH2:19][CH2:18]1)[CH3:22]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 591282733,5-Diethoxy-4-fluoro-benzaldehydeHCID 684569142,6-dimethyl-N-piperidin-4-yl-terephthalamic acid

Product 1

HCID 68454867N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-2,6-dimethyl-terephthalamic acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 2,6-dimethyl-N-piperidin-4-yl-terephthalamic acid (example 126b) 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: 472.9 (MH+).

Sources & evidence

ORD record
ord-37cac8a2be2f41948fd9beecf5e5ea7e
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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