Hydrochloric Acid → [6-[N-(4-Chlorophenyl)carbamoyl]-2-[4-[N-(4-chlorophenyl)carbamoyl]phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone Hydrochloride

HRID 1451998Notes

Reaction equation

HRID 1451998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]3[C:18]([C:19]([C:21]4[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH2:29][N:30]5[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]5)=[CH:23][CH:22]=4)=[O:20])=[C:17]([C:36]4[CH:41]=[CH:40][C:39]([C:42](=[O:51])[NH:43][C:44]5[CH:49]=[CH:48][C:47]([Cl:50])=[CH:46][CH:45]=5)=[CH:38][CH:37]=4)[S:16][C:15]=3[CH:52]=2)=[O:10])=[CH:4][CH:3]=1.C1COCC1.Cl>CCOCC>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:12]=[CH:13][C:14]3[C:18]([C:19]([C:21]4[CH:22]=[CH:23][C:24]([O:27][CH2:28][CH2:29][N:30]5[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]5)=[CH:25][CH:26]=4)=[O:20])=[C:17]([C:36]4[CH:41]=[CH:40][C:39]([C:42](=[O:51])[NH:43][C:44]5[CH:45]=[CH:46][C:47]([Cl:50])=[CH:48][CH:49]=5)=[CH:38][CH:37]=4)[S:16][C:15]=3[CH:52]=2)=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 18357247[6-[N-(4-Chlorophenyl)carbamoyl]-2-[4-[N-(4chlorophenyl)carbamoyl]phenyl]benzo[b]thien-3-yl][4-[2-(1piperidinyl)ethoxy]-phenyl]methanone

Product 1

HCID 70235393[6-[N-(4-Chlorophenyl)carbamoyl]-2-[4-[N-(4-chlorophenyl)carbamoyl]phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone HydrochlorideYield 122.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

4.01 g of [6-[N-(4-Chlorophenyl)carbamoyl]-2-[4-[N-(4-chlorophenyl)carbamoyl]phenyl]benzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]-phenyl] methanone was dissolved in 200 mL of ether and a small amount of THF added to affect solution. A solution of ether, which had been saturated with HCl, was added until no further precipitate formed. The reaction mixture was evaporated to dryness and triturated with ether several times. An attempt was made to crystalize the salt from hot EtOAc and absolute EtOH, which did work. Evaporation of the solvent, afforded 2.58 g of the title compound as a tan amorphous powder.

Workup

  1. additionwas added until no further precipitate
  2. customformed
  3. customThe reaction mixture was evaporated to dryness
  4. customtriturated with ether several times
  5. customto crystalize the salt from hot EtOAc and absolute EtOH, which
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9680f0979074433ca6a57a64fd573ebd
Source dataset
uspto-grants-1997_02
Patent number
US05605924

Reaction notes

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