Hydrochloric Acid → 1-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl diethylamino-acetate hydrochloride

HRID 2366446Notes

Reaction equation

HRID 2366446 reaction equation
[ClH:1].[CH2:2]([N:4]([CH2:7][C:8]([O:10][CH:11]1[CH2:16][CH2:15][N:14]([C:17]2[S:18][C:19](/[CH:22]=[C:23](\[C:34]#[N:35])/[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)=[CH:20][CH:21]=2)[CH2:13][CH2:12]1)=[O:9])[CH2:5][CH3:6])[CH3:3]>C(O)(C)C>[ClH:1].[CH2:2]([N:4]([CH2:7][C:8]([O:10][CH:11]1[CH2:12][CH2:13][N:14]([C:17]2[S:18][C:19](/[CH:22]=[C:23](\[C:34]#[N:35])/[C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH3:33])[CH:25]=3)=[CH:20][CH:21]=2)[CH2:15][CH2:16]1)=[O:9])[CH2:5][CH3:6])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 11964785YHO-13351 free base

Product 1

HCID 672278271-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl diethylamino-acetate hydrochlorideYield 70%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Isopropanol (10 mL) and 12N hydrochloric acid (59 μL) were added to Compound 103 (338 mg), and the mixture was heated for dissolution (external temperature: 80° C.). The solution was returned to room temperature, and allowed to stand overnight. The precipitated crystals were recovered through filtration, and the recovered crystals were recrystallized from isopropanol, to thereby yield the target product (yield: 254.5 mg, 70.0%).

Workup

  1. customwas returned to room temperature
  2. filtrationThe precipitated crystals were recovered through filtration
  3. customthe recovered crystals were recrystallized from isopropanol

Sources & evidence

ORD record
ord-beaf8c2abfb24d4490b8c8b91318414a
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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