Hydrogen Bromide → HCID 70392208, compound

HRID 1193680Notes

Reaction equation

HRID 1193680 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[C:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.Cl[CH2:23][CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH:33](C)[O:34][C:35]([C:37]2C=CC=CC=2)=O)=[CH:29][CH:28]=1.C(=O)([O-])[O-:45].[Na+].[Na+].[I-].[K+].[BrH:52]>C(O)CCC.C(O)(=O)C>[BrH:52].[CH2:35]([O:34][C:33](=[O:45])[C:30]1[CH:31]=[CH:32][C:27]([O:26][CH2:25][CH2:24][CH2:23][N:12]2[CH2:13][CH2:14][C:9](=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)[CH2:10][CH2:11]2)=[CH:28][CH:29]=1)[CH3:37]

Participants

8

Reactant 5

HCID 260Hydrogen BromideHCID 4875Potassium IodideHCID 10340Sodium CarbonateHCID 27244364-(Bis(4-fluorophenyl)methylene)piperidineHCID 53747374HCID 53747374, compound

Product 1

HCID 70392208HCID 70392208, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 2631-ButanolSolvent

Procedure

A mixture of 6.09 g (0.021 mole) of 4-[bis(4-fluorophenyl)methylene]piperidine, 5.20 g (0.02 mole) of 1-[4-(3-chloropropoxy)-phenyl]carbethoxybenzene and sodium carbonate 4.30 g (0.04 mole) in 230 ml of 1-butanol containing potassium iodide (0.3 g) was heated overnight at gentle reflux. The reaction mixture was stripped to dryness and partitioned between chloroform water and chloroform-5% sodium hydroxide. Removal of chloroform gave an oil. The oil was converted to the hydrobromide salt using hydrogen bromide in glacial acetic acid. The acetic acid and excess hydrogen bromide were removed in vacuo. The salt was recrystallized from methanol-diethyl ether. The salt was washed with water to remove acetamide present as an impurity. The salt was washed with diethyl ether and dried in vacuo overnight at 80° C. A yield of 6.81 g (59.5%) of white solid, m.p. 192°-194° C., was obtained.

Workup

  1. temperaturewas heated overnight at gentle reflux
  2. custompartitioned between chloroform water and chloroform-5% sodium hydroxide
  3. customRemoval of chloroform
  4. customgave an oil
  5. customThe acetic acid and excess hydrogen bromide were removed in vacuo
  6. customThe salt was recrystallized from methanol-diethyl ether
  7. washThe salt was washed with water
  8. customto remove acetamide
  9. washThe salt was washed with diethyl ether
  10. customdried in vacuo overnight at 80° C

Sources & evidence

ORD record
ord-36ea33585dd44919a0fef5b272920bd2
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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