N,N-Dimethylglycine hydrochloride → 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl dimethylamino-acetate p-toluenesulfonate

HRID 2366410Notes

Reaction equation

HRID 2366410 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[S:16][C:17]([N:20]3[CH2:25][CH2:24][CH:23]([OH:26])[CH2:22][CH2:21]3)=[CH:18][CH:19]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Cl.[CH3:28][N:29]([CH3:34])[CH2:30][C:31](O)=[O:32].O.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42]([OH:45])(=[O:44])=[O:43])=[CH:38][CH:37]=1>C1(C)C=CC=CC=1>[C:36]1([CH3:46])[CH:37]=[CH:38][C:39]([S:42]([OH:45])(=[O:43])=[O:44])=[CH:40][CH:41]=1.[CH3:28][N:29]([CH2:30][C:31]([O:26][CH:23]1[CH2:22][CH2:21][N:20]([C:17]2[S:16][C:15](/[CH:14]=[C:11](\[C:12]#[N:13])/[C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[CH:19][CH:18]=2)[CH2:25][CH2:24]1)=[O:32])[CH3:34]

Participants

5

Reactant 3

HCID 75605N,N-Dimethylglycine hydrochlorideHCID 521998p-Toluenesulfonic acid monohydrateHCID 16757522(Z)-2-(3,4-dimethoxyphenyl)-3-(5-(4-hydroxypiperidin-1-yl)thiophen-2-yl)acrylonitrile

Product 1

HCID 119656601-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl dimethylamino-acetate p-toluenesulfonateYield 7.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 6 (370 mg) was dissolved in toluene (80 mL), and N,N-dimethylglycin hydrochloride (140 mg) and p-toluenesulfonic acid monohydrate (380 mg) were added to the solution, followed by stirring under reflux for 5 hours. The solvent was evaporated to dryness, and the residue was purified by silica gel column chromatography (CHCl3-MeOH), to thereby yield the target product (yield: 38 mg, 7.7%).

Workup

  1. temperatureunder reflux for 5 hours
  2. customThe solvent was evaporated to dryness
  3. customthe residue was purified by silica gel column chromatography (CHCl3-MeOH)

Sources & evidence

ORD record
ord-4f951c6a5dee45ebb3ac711811975b2f
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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