Potassium Iodide → HCID 14407161, compound

HRID 1193694Notes

Reaction equation

HRID 1193694 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:15]2[CH:20]=[CH:19][C:18]([Cl: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]([C:33](=[O:35])[CH3:34])=[CH:29][C:28]=1[O:36][CH3:37].[I-].[K+]>C(O)CCC>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[C:9]2[CH2:14][CH2:13][N:12]([CH2:23][CH2:24][CH2:25][O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33](=[O:35])[CH3:34])=[CH:29][C:28]=3[O:36][CH3:37])[CH2:11][CH2:10]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 73142644-(3-Chloropropoxy)-3-methoxyacetophenoneHCID 144071724-[Bis(4-chlorophenyl)methylidene]piperidine

Product 1

HCID 14407161HCID 14407161, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 3.96 g (0.01305 mole) of 4-[bis(4-chlorophenyl)methylene]piperidine, 3.16 g (0.013 mole) of 1-[4-(3-chloropropoxy)-3-methoxyphenyl]ethanone in 300 ml of 1-butanol containing 0.3 g of potassium iodide 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 which crystallized from isopropyl alcohol. The solid was again crystallized from isopropyl alcohol to give 4.16 g (61%) of light yellow solid, m.p. 143°-144° C.

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 which
  5. customcrystallized from isopropyl alcohol
  6. customThe solid was again crystallized from isopropyl alcohol
  7. customto give 4.16 g (61%) of light yellow solid, m.p. 143°-144° C.

Sources & evidence

ORD record
ord-80f7b6b71ad047ceabcd0262ee0e0272
Source dataset
uspto-grants-1989_03
Patent number
US04810713

Reaction notes

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