Diisopropylethylamine → Rac-n-[1-(4-chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-(2,3-dihydroxy-propoxy)-5-methoxy-benzamide

HRID 502457Notes

Reaction equation

Cl.[OH:2][CH:3]([CH2:23][OH:24])[CH2:4][O:5][C:6]1[CH:7]=[C:8]([CH:18]=[C:19]([O:21][CH3:22])[CH:20]=1)[C:9]([NH:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:10].C(OC(N1CCCC(N(OCC2COCO2)C(=O)C2C=C(OC)C=CC2(C)C)C1)=O)(C)(C)C.Cl.O1CCOCC1.C(O[C:68](=O)[C:69]1[CH:74]=[C:73]([O:75][CH2:76][CH3:77])[C:72]([Cl:78])=[C:71]([O:79][CH2:80][CH3:81])[CH:70]=1)C.ClC1C(OCC)=CC(CN2CCC(NC(=O)C3C=C(OC)C=C(CO)C=3)CC2)=CC=1OCC.C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>CCO.C(O)(=O)C>[Cl:78][C:72]1[C:73]([O:75][CH2:76][CH3:77])=[CH:74][C:69]([CH2:68][N:15]2[CH2:16][CH2:17][CH:12]([NH:11][C:9](=[O:10])[C:8]3[CH:18]=[C:19]([O:21][CH3:22])[CH:20]=[C:6]([O:5][CH2:4][CH:3]([OH:2])[CH2:23][OH:24])[CH:7]=3)[CH2:13][CH2:14]2)=[CH:70][C:71]=1[O:79][CH2:80][CH3:81]

Participants

Procedure

In analogy to the procedure described in example 50k), rac-3-(2,3-dihydroxy-propoxy)-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride (prepared from rac-4-[3-(2,2-dimethyl-[dioxolan-4-ylmethoxy)-5-methoxy-benzoylamino]-piperidine-1-carboxylic acid tert-butyl ester (example 175a) by reaction with HCl/dioxane in EtOH in analogy to the procedure described in example 250b)] was reacted with 4-chloro-3,5-diethoxy-benzaldehyde (example 219), sodium cyanoborohydride, N-ethyl-diisopropylamine and acetic acid in ethanol at 50° C. to yield the title compound as light brown solid. MS: 537.4 (MH+).

Sources & evidence

ORD record: ord-1805e5d9ccf44c06b1a8d948d3ae816d
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07772253B2

Reaction notes

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Reaction equation

Participants

Reactant 6

Product 1

Reagents, catalysts & solvents 2

Procedure

Sources & evidence

Reaction notes