Potassium Iodide → HCID 21433532, compound

HRID 596293Notes

Reaction equation

HRID 596293 reaction equation
Cl.[CH2:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]21[CH2:16][CH2:15][CH:14]([NH:17][CH3:18])[CH2:13][CH2:12]2.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl:27][CH2:28][CH2:29][CH2:30][C:31]([C:33]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=1)=[O:32]>CN(C)C=O>[ClH:27].[F:39][C:36]1[CH:37]=[CH:38][C:33]([C:31](=[O:32])[CH2:30][CH2:29][CH2:28][N:17]([CH:14]2[CH2:15][CH2:16][C:3]3([CH2:4][CH2:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:2]3)[CH2:12][CH2:13]2)[CH3:18])=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 21433642HCID 21433642, compound

Product 1

HCID 21433532HCID 21433532, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the free base prepared from 0.81 g. of 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl-N-methylamine hydrochloride [I(c)] (obtained as in Example 14C), 0.63 g. of potassium iodide, 0.96 g. of potassium carbonate and 0.87 g. of the 2,2-dimethyl-1,3-propanediol ketal of 4-chloro-4'-fluorobutyrophenone in 15 ml. of dimethylformamide is heated together in an oil bath at about 90° C. for about 20 hours. The solvent is removed under vacuum and the residue dissolved in water and benzene. The organic layer is washed with water and brine and evaporated to dryness. A mixture of the residue, 6 ml. of 2.5 N hydrochloric acid and 12 ml. of methanol is stirred at room temperature for about 1.5 hours and most of the methanol removed under vacuum. The residual suspended solid is collected on a filter, washed with ether and recrystallized from methanol: ethyl acetate to give 4'-fluoro-4-[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl-N-methylamino]butyrophenone hydrochloride [I(c)].

Workup

  1. additionA mixture of the free base
  2. customprepared from 0.81 g
  3. customThe solvent is removed under vacuum
  4. dissolutionthe residue dissolved in water
  5. washThe organic layer is washed with water and brine
  6. customevaporated to dryness
  7. additionA mixture of the residue, 6 ml
  8. customremoved under vacuum
  9. customis collected on a filter
  10. washwashed with ether
  11. customrecrystallized from methanol

Sources & evidence

ORD record
ord-978856255dad47379020377938e69fc5
Source dataset
uspto-grants-1977_03
Patent number
US04010201

Reaction notes

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