Diisopropylethylamine → N-[1-(4-Chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-hydroxy-5-methoxy-benzamide

HRID 502465Notes

Reaction equation

HRID 502465 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:26]=[C:27]([O:30][CH2:31][CH3:32])[C:28]=1F)[CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:25])[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([OH:24])[CH:17]=2)[CH2:10][CH2:9]1)[CH3:2].C(OC(=O)C1C=C(OCC)C([Cl:46])=C(OCC)C=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>C(O)C.C(O)(=O)C>[Cl:46][C:28]1[C:4]([O:3][CH2:1][CH3:2])=[CH:5][C:6]([CH2:7][N:8]2[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:25])[C:16]3[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([OH:24])[CH:17]=3)[CH2:10][CH2:9]2)=[CH:26][C:27]=1[O:30][CH2:31][CH3:32]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 68455428N-[1-(3,5-Diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-3-hydroxy-5-methoxy-benzamideHCID 68456709N-[1-(4-Chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-hydroxymethyl-5-methoxy-benzamide 4-Chloro-3,5-diethoxy-benzoic acid ethyl ester

Product 1

HCID 68456085N-[1-(4-Chloro-3,5-diethoxy-benzyl)-piperidin-4-yl]-3-hydroxy-5-methoxy-benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 3-hydroxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride (example 257) 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 colorless amorphous solid. MS: 463.3 (MH+).

Sources & evidence

ORD record
ord-59f11216ccfe483e805bd9a09410c75c
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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