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

HRID 502461Notes

Reaction equation

HRID 502461 reaction equation
Cl.[C:2]([CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11])(=[O:4])[NH2:3].[CH2:24]([O:26][C:27]1[CH:28]=[C:29]([CH:32]=[C:33]([O:36][CH2:37][CH3:38])[C:34]=1[F:35])[CH:30]=O)[CH3:25].C([BH3-])#N.[Na+].C(N(C(C)C)C(C)C)C>C(O)C.C(O)(=O)C>[C:2]([CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1)[C:10]([NH:12][CH:13]1[CH2:14][CH2:15][N:16]([CH2:30][C:29]2[CH:32]=[C:33]([O:36][CH2:37][CH3:38])[C:34]([F:35])=[C:27]([O:26][CH2:24][CH3:25])[CH:28]=2)[CH2:17][CH2:18]1)=[O:11])(=[O:4])[NH2:3]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5003444Sodium cyanoborohydrideHCID 591282733,5-Diethoxy-4-fluoro-benzaldehydeHCID 684580663-carbamoylmethoxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride

Product 1

HCID 684577883-Carbamoylmethoxy-N-[1-(3,5-diethoxy-4-fluoro-benzyl)-piperidin-4-yl]-5-methoxy-benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 50k), 3-carbamoylmethoxy-5-methoxy-N-piperidin-4-yl-benzamide hydrochloride 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: 504.3 (MH+).

Sources & evidence

ORD record
ord-9cace687e6e24960a28536cecaa384f7
Source dataset
uspto-grants-2010_08
Patent number
US07772253B2

Reaction notes

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