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 1604487Notes

Reaction equation

HRID 1604487 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-8bcdac2fc075427693586a97dd8b1908
Source dataset
uspto-grants-1999_11
Patent number
US05994371

Reaction notes

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