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Potassium Iodide → 4'-fluoro-4-[[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]amino]butyrophenone hydrochloride

HRID 2398815
Notes
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Reaction equation

HRID 2398815 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]([NH2:17])[CH2:13][CH2:12]2.[I-].[K+].C(=O)([O-])[O-].[K+].[K+].[Cl:26][CH2:27][CH2:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)=[O:31]>CN(C)C=O>[ClH:26].[F:38][C:35]1[CH:34]=[CH:33][C:32]([C:30](=[O:31])[CH2:29][CH2:28][CH2:27][NH:17][CH:14]2[CH2:13][CH2:12][C:3]3([CH2:4][CH2:5][C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[CH2:2]3)[CH2:16][CH2:15]2)=[CH:37][CH:36]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 197503-(4-Fluorobenzoyl)propyl chlorideHCID 122512743',4'-Dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride

Product 1

HCID 122512764'-fluoro-4-[[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]amino]butyrophenone hydrochlorideYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The free base from 1.65 g. (0.0066 M) of 3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-ylamine hydrochloride [I(c)] (prepared in Example 10C), 1.34 g. of potassium iodide, 2.06 g. of potassium carbonate and 1.9 g. of the 2,2-dimethyl-1,3-propanediol ketal of 4-chloro-4'-fluorobutyrophenone in 35 ml. of dimethylformamide are heated in an oil bath at about 90° C. for about 18 hours. The solvent is removed under vacuum and the residue that remains is dissolved in benzene and water. The organic layer is washed with water and brine and evaporated to dryness. A mixture of the residue and 10 ml. of 2.5 N hydrochloric acid in 20 ml. of methanol is stirred at room temperature for about 4 hours. The methanol is then removed under vacuum and the solid collected on a filter. This material is recrystallized twice from methylene chloride: ethyl acetate to give 1.07 g. (39% yield) of 4'-fluoro-4-[[3',4'-dihydrospiro[cyclohexane-1,2'(1'H)-naphthalen]-4-yl]amino]butyrophenone hydrochloride [I(c)], having a melting point of 182° to 184° C.

Workup

  1. customThe solvent is removed under vacuum
  2. dissolutionthe residue that remains is dissolved in benzene
  3. washThe organic layer is washed with water and brine
  4. customevaporated to dryness
  5. additionA mixture of the residue and 10 ml
  6. customThe methanol is then removed under vacuum
  7. customthe solid collected on a filter
  8. customThis material is recrystallized twice from methylene chloride
  9. customethyl acetate to give 1.07 g

Sources & evidence

ORD record
ord-e6f46eea0f254627bdf214acfede0c92
Source dataset
uspto-grants-1977_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04025558

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes