Acrylic Acid → 3-[4-(4-Amino-5-chloro-2-methoxy-benzoylamino)-3-methoxy-piperidin-1-yl]-propionic acid

HRID 1267144Notes

Reaction equation

HRID 1267144 reaction equation
[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1.[C:22]([OH:26])(=[O:25])[CH:23]=[CH2:24]>ClCCl>[NH2:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]([C:6]([NH:8][CH:9]2[CH2:14][CH2:13][N:12]([CH2:24][CH2:23][C:22]([OH:26])=[O:25])[CH2:11][CH:10]2[O:15][CH3:16])=[O:7])=[C:4]([O:20][CH3:21])[CH:3]=1

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 3019427Norcisapride

Product 1

HCID 185459953-[4-(4-Amino-5-chloro-2-methoxy-benzoylamino)-3-methoxy-piperidin-1-yl]-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-amino-5-chloro-2-methoxy-N-(3-methoxy-piperidin-4-yl)-benzamide (1 g, 3.2 mmol), and 241 μL of acrylic acid in 50 ml dichloromethane was stirred under nitrogen for 6 hr then concentrated in vacuo. The residue was slurried with hot ethyl acetate and filtered at room temperature to yield 1.15 g of product as a white solid.

Workup

  1. concentrationthen concentrated in vacuo
  2. filtrationfiltered at room temperature

Sources & evidence

ORD record
ord-ceba65061c6b4ad3a7b2b697fffc804e
Source dataset
uspto-grants-2003_04
Patent number
US06552046B2

Reaction notes

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