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 325160Notes

Reaction equation

HRID 325160 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.O1CCCC1.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 tetrahydrofuran added to affect solution. A solution of ether, which had been saturated with hydrogen chloride, 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 ethyl acetate 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 ethyl acetate and absolute EtOH, which
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ba724d2d26044fd0a187ba0fe764d88b
Source dataset
uspto-grants-2001_04
Patent number
US06221838B1

Reaction notes

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