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

HRID 2366445Notes

Reaction equation

HRID 2366445 reaction equation
[ClH:1].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:13][N:14]([CH2:16][C:17]([O:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28](/[CH:31]=[C:32](\[C:43]#[N:44])/[C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH3:42])[CH:34]=3)=[CH:29][CH:30]=2)[CH2:22][CH2:21]1)=[O:18])[CH3:15]>C(O)C>[ClH:1].[CH3:13][N:14]([CH2:16][C:17]([O:19][CH:20]1[CH2:21][CH2:22][N:23]([C:26]2[S:27][C:28](/[CH:31]=[C:32](\[C:43]#[N:44])/[C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[C:35]([O:41][CH3:42])[CH:34]=3)=[CH:29][CH:30]=2)[CH2:24][CH2:25]1)=[O:18])[CH3:15]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 119656601-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl dimethylamino-acetate p-toluenesulfonate

Product 1

HCID 672288061-[5-[(Z)-2-cyano-2-(3,4-dimethoxy-phenyl)-vinyl]-thiophen-2-yl]-piperidin-4-yl dimethylamino-acetate hydrochlorideYield 48.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Ethanol (5 mL) and 12N hydrochloric acid (28 μL) were added to Compound 62 (150 mg), and the mixture was heated for dissolution (external temperature: 40° 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: 78.7 mg, 48.6%).

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-476faeea5d274bd8831b1a9b31213a65
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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